


Control and Release

by CleverDame



Category: Supernatural
Genre: AU!Sam, Anal Play, Anal Sex, Bondage and Discipline, Breathplay, Dom/sub, Dominance, Dubious Consent, F/M, Humiliation, Kale!SAm, Loss of Control, Mutual Masturbation, Nipple Clamps, Nipple Play, Public Humiliation, Rape/Non-con Elements, Rough Oral Sex, Shame, Smut, Spanking, Vaginal Fingering, Vaginal Fisting, Vaginal Sex, au!samwinchester
Language: English
Status: In-Progress
Published: 2019-02-12
Updated: 2019-10-08
Packaged: 2019-10-26 22:45:24
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 24
Words: 86,483
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17754920
Author URL: https://archiveofourown.org/users/CleverDame/pseuds/CleverDame
Summary: After the rest of the staff is caught in a snowstorm, you find yourself acting as a personal assistant to the notorious Sam Winchester. As the arrangement becomes more defined, you and Sam begin a sexual adventure with dangerous consequences.  - This fic is based on Ted Talk Sam S14x13





	1. One

-

“No way!” You close your eyes. This has to be a nightmare.

“You’re the only person who made it to the hotel. We’re all snowed in until morning, no one can get a flight out. You’re going to have to staff him until I get there. His schedule is pretty light compared to what it usually looks like. Half his meetings were canceled because of the storm.” Pepper rattles into the phone. She’s only a year or two older than you but she’s your boss’s boss. She’s Sam’s executive assistant, in charge of the entire assistant staff and she’s had it out for you since you started four months ago.

“I don’t think I can do this.” You gulp, shrugging your jacket off. You deliver mail and push the coffee cart around the building, the lowest rung on the corporate ladder.

“You don’t have a choice.” She snips. “You think this is what I want? I’m going to end up paying for this, even though it’s not even remotely my fault. I can’t control the weather…look I’m going to send you his schedule.  Just make sure he’s on time. He’ll let you know if you’re doing something wrong, believe me. Just keep your mouth shut and do what he tells you to do. Whatever you do, don’t cry. He hates it when people cry.”

“Why would I cry?” You regret answering the phone and you already know the answer to your question.

Sam Winchester is a real son-of-a-bitch and everyone knows it.

To say his reputation proceeds him would be a gross understatement. He’s smart, successful, ruthless and above all, focused. You’ve worked for Winchester and Singer for six months and have yet to encounter him.

You’ve never even directly spoken to him, never seen him in person other than the monthly reviews he conducts with the entire company in attendance. Even then he’s just a man on a stage.

“I’m emailing you right now. Keep a copy of the schedule on you at all times.” She pauses to take a breath. “Are you listening to me?”

“Yeah, I’m listening. Have the schedule on hand, keep my mouth shut, and try not to burst into tears.”

“Just don’t fuck this up.” Pepper is as over-worked as everyone on the executive level. You can’t really blame her. This job is her life. “You need to check in with him tonight. Just knock on his door and ask if he needs anything. He’ll send you away, but he expects a check in just to be sure.”

“Okay.” You nod to yourself in a windowless hotel room. “I can do this.”

-

The elevator rises slowly to the penthouse floor of the Ambassador Hotel. It’s nearly midnight and his flight arrived only an hour ago. He was in Tokyo last week and was rerouted during the storms in Boston.

You knock twice on his door, waiting with bated breath and hoping he won’t answer. You’re about to leave when the deadbolt turns and the door opens to reveal Sam Winchester with a cell phone up to his ear. He pauses for a moment, looking you over head to toe before opening the door the rest of the way and walking away chattering to whoever is on the other line.

You stand in the hallway, unsure if the open door is an invitation. On cue he turns around, eyes narrowing as his nods his head.

Already off to a rough start.

Shutting the door behind you, you follow him into the living room, standing awkwardly, waiting for his call to end. When he finally hangs up, he presses his phone against his chest, staring at you like a zoo animal. “Pepper said you’re the only employee here?”

“Y-yes.” You choke out. “I was visiting family in New Mexico, so I flew in from-”

“We’ll have to make due I guess.” He cuts you off. “You have tomorrow’s schedule?”

“Ahuh.” You hold up your phone, forcing a smile.

“Ahuh?” He tilts his head. “I prefer actual words. Yes or no.”

Your cheeks flush hot, embarrassment settling in.

“Yes, Mr. Winchester.” You correct. “I have your schedule. Pepper asked me to check in and see if you need anything tonight.”

“No. I don’t need anything.” His stare is unrelenting. “Do you have something more appropriate to wear tomorrow?”

His question takes you off guard as you look down at the sweatshirt and jeans you’re currently wearing. “I, um, yes sir.”

There’s a nauseating combination of shame and anger settling into your gut. He really does live up to his reputation.

“Good. You better go. We have an early start tomorrow. I won’t need you until after the gym. I’ll be done by 6:15 and I expect you to be here.”

“Yes, sir.” You nod, looking at anything but his face. You’re an ant under a microscope, already feeling the heat.

“Good. You can go now.” He pulls out his phone, hits a number and begins speaking to someone in Japanese as you high tail it out of the room.

You don’t cry until you’re in the elevator. The doors shut as you fight back the urge to turn into a sobbing mess, instead of wiping away a few tears and composing yourself.

Three hours of sleep is all you manage. Between your nerves and being afraid you’ll sleep through the alarm, you’re up and showered at four and dressed by five.

Clutching a portfolio in your arms you step off the elevator. There’s a full-length mirror at the end of the hallway and you stop to make sure you’re presentable. You thought you’d be manning a promotional table during the conference, planned on wearing khakis and a pullover. You brought exactly one business professional outfit that you haven’t tried on in a year or two. It’s a plum-colored sleeveless sheath dress that’s tighter than you would prefer. It looks good but perhaps a little much for this trial by fire.

“This is as good as it gets.” You whisper, giving yourself a final look before finding Sam’s room.

You knock and he answers immediately, holding his glasses in hand.

“You’re late.” He quips, turning around to gather his suit jacket and briefcase.

“I,” You stop, checking your phone. “It’s 6:15.”

“In my world on time is late and early is expected.”

“I’m sorry.” You’re horrified. “I didn’t - I’m sorry.”

“I don’t want an apology. I want you to do better next time.” He eyes settle on your bare shoulders, then tick down to rest of your body. It’s a quick glance but you catch him. “I have files in the living room. Please make sure everything is in order and ready to go. Pack it all up, we don’t want to leave anything to chance.”

You wordlessly scamper around the room, carefully collecting half used notepads and countless pages of legal discourse that you couldn’t understand if your life depended on it. When you turn back around, clutching his files in your arms, he’s leaning against the doorframe between the entryway way and the living area, watching you intently.

Your cheeks burn hot. Sam is handsome, there’s no arguing that fact, but he’s also notoriously difficult to work for. You’ve never once heard even a whisper that he mixes business with pleasure. If anything he’s known for being controlled. Everyone’s heard of his type, high-level business execs that are uptight beyond belief.

But the way he’s looking at you…no. It’s in your head.

“I’ve got everything.” You nod, shoving the files into your leather bag.

“Good, I want to get down there early.” He checks his watch and strides out of the room without another word and you’re left scrambling after him. Instead of heading to the public elevator you took earlier, he turns in the opposite direction to head toward the private lift his penthouse room offers as a perk. You stand beside him as the doors close and he pushes the button for the ground level.

He turns toward you, looking concerned. “I asked you to wear something business professional.”

“I-” The humiliation continues. “I am. This is all I brought with me.”

“I see.” His eyes narrow.

“Would you like me to go grab a sweater to wear over it?” You ask softly.

“No.” He purses his lips, head tilting ever so slightly. “I wouldn’t be able to tell how tight your dress is if I couldn’t see your panty line.”

You nearly choke on your own spit. Letting out a nervous cough as your breath speeds up. You force yourself to look at him, trying your damnedest to determine what this is. Is he coming on to you? Just a perfectionist who’s so caught up in the details that the outline of your lace underwear crosses some sort of invisible line?

“I didn’t realize you could see. I’m sorry.” You stare at the floor, praying to God this day ends quickly.

“Don’t be sorry.” He commands tone calm and even. “Take them off.”

The world stops. All the oxygen evaporates out of the room.

Your eyes go wide, shooting up to meet him and his expression is unreadable. In a split second, your body reacts against your will, heat blooming between your legs, shame tightening in your chest.

You wonder if he’s like a predator able to smell fear. Does he somehow know what kind of effect this will have on you? Is it the way you called him sir, or how quickly you responded to his commands?

“You want me to…” You can’t finish the sentence but he doesn’t need you to.

“Take them off.” He repeats.

“Right now…here?” You whisper.

“Yes.” He confirms, reaching out to take the bag from you.

You hesitate, but only for a second before reaching under your dress and hooking both hands in your panties. The elevator is nearly at the first floor, and sweat breaks out over your entire body at the idea of being caught.

Stepping out of your panties you hold them up, looking at him like a deer in the headlights. There’s nowhere to put them, you didn’t bring a purse, the conference is in the hotel so you left it the room. But Sam casually plucks them from your hand and stuffs them into the pocket of his suit pants as the elevator reaches the lobby and the doors slide open with a ding.

“Try to keep up.” He hands you back his briefcase, your messenger bag of files, and steps out into the general population as you follow.


	2. Two

You’re sitting next to Sam Winchester, the man that Forbes called  _ one of the most powerful men in business _ ...and he’s got your panties tucked in his pocket like it’s no big deal. 

 

For the last twenty minutes, you’ve been gaslighting yourself. 

 

Maybe you read the situation wrong? What if he didn’t even mean for you to take off your underwear in the elevator? But the more you replay the incident over and over in your mind you know it really happened. It’s a fact that's only confirmed as you shift in the chair and feel your naked ass against the fabric of the dress. 

 

“Y/N.” It’s Sam saying your name and snapping his fingers that brings you out of this daze. 

 

“I’m so sorry.” You gasp, staring from Sam to the other man in the room.

 

“Do we have the third quarter prospectus or not?” Sam raises his eyebrow and you fish through the folder in front of you. 

 

“Yes.” Sliding a copy of the analysis toward both men. “There are future projections on the second page.” 

 

You’ve memorized every detail of the emails Pepper sent. While you don’t understand the actual content, you've at least memorized what each meeting requires. 

 

“Thank you.” Sam’s tone is less than understanding and the man across the table chuckles. 

 

“What happened to your old assistant.”

 

“She’s couldn’t be here.” Sam’s eyes don’t leave the report in front of him as they talk about you like you’re not even here. “We’re just working with whatever asset we have, however poor that may be.” 

 

The guy snorts and you turn beet red, fight back a swell of emotion. He’s just...mean. 

 

You listen to them drone on and on about the future of intellectual property rights and their shared hatred for Jeff Bezos. It’s almost one o’clock by the time the meeting is wrapping up. That leaves an hour before he needs to meet with his financial team, the first employees on the ground since the storm passed. 

 

“Are you hungry?” Sam asks succinctly, taking off his glasses and tucking them into his suit jacket. 

 

“Yeah - I mean, Yes. I’m starving.” You collect his handwritten notes, carefully packing them into his briefcase. 

 

“Good, we’ve got time to sit down for a meal. The restaurant here is supposed to be at least tolerable.”

 

\--

 

Sam’s enthralled with his phone and you’re just happy to have his attention elsewhere. You watch as the wait staff carries trays of food in both directions. You haven’t eaten in twenty-four hours and all you want is the juicy burger that just walked by.

 

Your waiter is a young, happy guy who bounces over to the table. While he might not know who Sam is, he knows money when he sees it, occupational hazard. 

 

“Welcome.” He clasps his hands together. Sam sets his phone on the table, offering his full attention. “Can I get you started with a drink? We have several white wines that are perfect for a light lunchtime-”

 

“No,” Sam grimaces. “Two waters and we’ll need to order now. We’re on a tight schedule.”

 

“Sure, of course.” The waiter gestures toward the menu. He turns toward you, “Do you know what you’d like ma'am?”

 

You can practically taste the burger. “Definitely, I want-” 

 

“She’ll have the blood orange and spinach salad, and I’ll have red quinoa and avocado.” Sam looks across the table, closing his menu. The waiter hesitates, looking between you and Sam, who clears his throat. “That’s all.”

 

You sit back in your seat, clenching your fist under the table. What is this? Your first instinct is that this a test. He’s systematically testing your limits like a raptor testing the fence in Jurassic Park. He wants to see how far he can push. His comments about your clothes, the panties, his snide remarks in the meeting and now ordering your lunch - he wants to find out how much you’ll take. 

 

It’s his motives you’re unsure about. Is he interested in you sexually or is all this just his sick version of a power game?

 

“Thank you,” you smile sweetly. “I was going to order a salad but I couldn’t decide which one.”

 

His eyes narrow, resting a forearm on the table. “It’s important to take care of your body.”

 

There it is, something dark simmering right under the surface This guy has boatloads of pent up issues, he’s going to make some therapist a lot of money one day. 

 

“I agree.” You sit up straight, folding the cloth napkin over your lap. 

 

“Do you?” He’s grinning but his eyes are honed in on you like a snake sizing up a fat little mouse. “Do you exercise?”

 

“Ye- _ yes _ .” You catch yourself this time. Normally you’re pretty good at faking confidence when you can’t muster the real thing but Sam is getting under your skin. “I used to be a runner, but I hurt my knee a couple years back. Now it’s all pilates and yoga.”

 

“How old are you?” His thumb and middle finger slide over each other as his studies you.

 

“Twenty-eight.” You take a drink of water just to break the intensity of his focus. 

 

“And how did you end up working for me?” 

 

“I just, I needed some office experience. I’ve never really worked in a professional environment before. I’m just trying to get my life on track, or least headed one solid direction. Look, I shouldn’t be here. I deliver the mail. I’m no one, Mr. Winchester.”

 

His throat bobs when you call him  _ Mr. Winchester _ , a smile tugging at the corners of his mouth. 

 

“I think you’re someone.” His eyes drag over you again, like you’re a piece of meat. There is no mistaking he wants something more from you than note taking. “Do I make you nervous?”

 

“Yes.” You respond succinctly. “I don’t know what you want - I’m not sure how to react.”

 

“You’re doing fine so far.” 

 

“Yeah, right,” you sigh, looking up at the ceiling. “I’m terrible at this. I’m not organized, I don’t know what I’m doing and you have standards that are beyond-”

 

“I don’t care about that.” He waves his hand, that calm demeanor never breaking. “You’re not the most organized assistant, but Pepper will be here by tonight. She’ll fix whatever you manage to fuck up.”

 

You swallow, staring in silence as a waitress brings your salads. Once you’re alone again you lean in closer, placing both hands palm down on the table. “Why are you doing this?”

 

“What am I doing?” He asks, forking leafy greens, glancing up as an afterthought. 

 

“The way you talk to me. In the elevator when you -” You whisper, making sure no one can hear you. “You have my underwear in your pocket.” 

 

“Do you need them back?” He sets down his fork.

 

“What?” That wasn’t the response you expected. 

 

“If you need them, I’ll give them to you.” He offers. 

 

“I don’t understand this. You’re...” your point at him. “ _ You. _ You don’t know anything about me. I could sue you for sexual harassment.”

 

“Are you going to sue me?” He’s clearly unconcerned. “Let me ask you a question, Y/N. Why do you think I’ve been so successful?” 

 

Clasping hands together in your lap you think carefully, trying to suss out if this was a trick question. “You’re smart, focused. You work hard.”

 

“None of those really matter in the long run. The reason I’ve gotten to where I am today is that I can read people. My dad was a ringer, but I’m even better at it. You give me two minutes with anyone and I’ll tell you what you want and if they’re telling the truth. Everyone has a tell, it’s the little ticks and unconscious responses that give people away.” 

 

“Like poker.” You add and he seems happy you made the connection. 

 

“Yes, something like that. Last night when you came to my room you were nervous, unsure of yourself. But the moment I corrected you, told you to  _ use your words _ , you start breathing faster, pupils dilated. You do the same thing every time you call me Mr. Winchester.” 

 

“In the elevator, it was more than just your eyes and your breath. Your whole body went flush and lips parted. Every inch of you liked being given orders. You see, most people don’t like how direct I am. I hurt feelings, burn a lot of bridges. But you are a rare creature. You enjoy the degradation.” 

 

“Well,” you start, closing your eyes in a flawed attempt to keep your cheeks from burning bright red. “I don’t know that I would say I  _ enjoy _ it.”

 

“Tell me,” he pulls back a little, talking to you as if you’re the only two people in the room. “Are you wet right now?”

 

The question alone makes your thighs clench together. You stare at him for a moment before answering. 

 

“Yes.” The confession comes out as a whimper. 

 

He smirks, refocusing on his meal. “Eat your lunch. We have a long afternoon.” 

 

-

 

After seven hours of meetings and glad-handing, you’re grateful the day is coming to an end. Everyone wants to meet Sam, talk to him, pitch their ideas and make a connection. Everyone wants a piece of him and you’ve spent the day trying to note down the name and position of every person he spoke to. 

 

It’s a little after eight as you trail behind him, lugging his briefcase back up to his room. 

 

“Pepper’s here.” He looks up from his phone, fishing his room card from his pocket. “She’ll take over for the cocktail hour tonight.”

 

“Perfect.” You sigh. You weren’t sure you had the stamina to make it through the rest of the night.

 

“Do you want to come inside?” He asks, pushing the door open, stepping out of the way. 

 

“No.” You avoid his eyes. “I’m gonna go to my room.”

 

“Are you sure?” His head tilts to the side. 

 

“Yes.” You carefully set his briefcase at his feet. “Goodnight.”

 

“Y/N.” He says your name with such finality that it sends a shiver up your spine. “Come inside.”

 

“I said I dodn’t want to.” You meet his stare as your hands begin to shake. “We shouldn’t-“

 

“And I told you to come inside.” His jaw clenches when you hesitate. “Now.”

 

“Okay.” You squeak stepping into the room. The door shuts behind you immediately, and there’s the click of the deadbolt. 

 

“In here.” He disappears through a doorway and you follow into the master suite. The moment you lay eyes on his bed a warmth bubbles up from your belly. You hate that there’s any part of you that responds to him like this. 

 

Sam circles around you, keeping his distance as he takes a seat in the chair in the corner of the room.

 

“What do you want from me?” You ask, barely able to stand on quivering legs. 

 

“I want you to sit on the bed.” He explains, leaning back in the chair. His mouth is a tight line, betraying nothing. If he has any particular feelings one way or the other you’d be the last to know. 

 

“Okay.” You whisper, sitting gingerly on the edge of the bed, watching him watch you. 

 

“Unzip your dress.” His instruction is enough to take the air right out of your chest. He must be enjoying this level of control, but you’d never know from looking at him. 

 

You reach behind your shoulders and manage to unzip the back, looking to him for further orders. 

 

“Pull it down around your waist.” One large hand palms over the crotch of his slacks, giving the first indication that he’s getting any actual pleasure. 

 

You comply, pulling your arms out and lowering the top half of the dress until it’s bunched below your breasts, exposing a lace, black bra. 

 

“Pull your bra down. Show me your nipples.” His eyes shift down to watch.

 

_ Oh, God.  _

 

You tug each cup down until both breasts are exposed. Your nipples are already hard as pebbles, aching along with the rest of your body. 

 

“Pull your skirt up around your thighs.” He watches as your eyes fall to his hand, rubbing his cock through his pants. You comply, pulling your skirt up. “Further.” 

 

By the time he’s satisfied your dress is up around your hips, bare ass on the soft comforter.

 

“Now lie back and spread your legs.” 

 

You stare at each other for a moment before you lean back, the back of your head meets the mattress. You suck in a fractured breath, spreading your thighs until you feel the cool air on your sex. 

 

“Wider.” He’s a disembodied voice now. Measured and confident in every detail of what he wants from you. “Let me see your pussy.”

 

You bend your knees, putting your heels on the bed until they touch your buttocks, spreading yourself as wide as possible for his viewing pleasure. 

 

“Your cunt’s as perfect as the rest of you.” He laments, but you get a distinct feeling he’s not really talking to you, it’s just commentary. “Touch yourself.”

 

You close your eyes for a moment, the ceiling blinking in and out of view as your hand snakes between your legs. Using your middle finger you find your clit and make slow, careful circles, applying just enough pressure to bring yourself pleasure. 

 

This is by far the most humiliating thing you've ever done, but it's the humiliation that has you so worked up. He was right. There’s something about the complete shame of the moment that’s working you up. 

 

There’s a familiar  _ zip _ and the rustle of clothing, and then the faint, subtle sound of skin on skin as he strokes his cock, watching you masturbate. 

 

The more your body responds, the less you care about the fact that you’re rubbing your clit in front of your boss. Dipping into your slick cunt, you coat your finger, moving back to press faster circles over the swollen bud. A muted sigh escapes your lips and you realize you’ve been trying to stay quiet but there’s no reason remain silent. A full moan tears from your throat as you butterfly your legs further apart in an effort to give a better view. At this moment you want him to see every inch of you, to feel his eyes burning into your skin. 

 

“Fuck yourself with your fingers.” His voice is strained, a crack in the armor as you hear him stroke himself faster. 

 

You slide your other hand between two shaking thighs and sink two fingers into your pussy. He’s breathing faster, harder and the room is filled with the sounds of both your labored breath, the wet noise of your cunt taking your own fingers and Sam working his cock. 

 

“Oh fuck.” You moan, arching back into the mattress and shoving a third finger into your aching cunt. Your hand is moving faster and faster over your clit and you’re  _ so close _ to having an orgasm in front of his man you hardly know. 

 

“Put the fingers that are in your cunt, in your mouth, and keep rubbing your clit. Make sure your legs stay open when you cum.” He pants, the  _ whap, whap, whap _ of his hand growing even faster. 

 

You don’t hesitate, shoving the three fingers over your tongue, sucking on the taste of yourself as you cum. Groaning, you struggle to keep your thighs spread wide, giving him a full view of your wet, empty flesh clutching around nothing. 

 

He grunts one time, and the sound of his hand stops as you claw at the sheets, trying to anchor yourself as you pant and stare at the ceiling. 

 

For minutes the only sound is your breath. You’re not sure what to do, but then he’s zipping up as you hear him moving across the floor. “You can leave.”

 

By the time you sit up, he’s gone. The door to the bathroom clicks shut, the lock turns as the shower comes on. Leaving you trembling and unsure of what exactly just happened. 


	3. Three

Life goes on, you return to Boston but the events of that night haunt you. There are times when you can’t believe it actually happened, that Sam Winchester had you in his room. And there are nights when it’s all you can think about, laying in the dark with a hand between your legs pretending he’s watching you.

But a week becomes a month and you get the sense that whatever happened was a fleeting mistake. A questionable choice that he’d prefer to forget.

You’re in the middle of typing up handwritten notes for one the of the junior partners when the phone rings. Pepper’s name pops up and you roll your eyes. She hated you from the beginning but after the conference, she’s really had it out for you. She made it clear that you did everything wrong, and she suffered Sam’s sour disposition as a result.

“Hello Pepper,” you answer, feigning a cheery disposition.

“What did you do?” She hisses, clearly trying to keep her voice down.

“I don’t know what that means.” You slouch back in your chair, defeated. None of your work is ever good enough for her.

“Well, you better figure it out. He wants you up here,  _now_.” She grits out.

An immediate mix of dread and excitement springs to life, making your chest tight and cheeks flushed. Before even fully processing the words, you’re sweating.

“Who?” Whispering, you look around, afraid that anyone who sees you might suddenly develop telepathic powers and discover your dirty little secret.

“Who the fuck the do you think?  _Sam_. I don’t know what you did but he wants you in his office ASAP.”

“Okay.” You swallow. “I’m on my way.”

The walk to the elevator seems as if you’re walking underwater, everything moving in slow motion. You’ve convinced yourself you’d never see him in person again, or when you did, he’d dismiss you.

What if this is just about work? No, there’s no way. You’re in charge of the most meaningless, mindless busy-work of anyone in the company. This is him flexing control, you’re sure of it. He’s ignored you for weeks and out of nowhere, you’re being summoned to the executive floor.

“You okay?” Max, a junior associate, and resident hot shot asks stepping in beside you.

“Yeah.” You snap, looking at him in sudden concern. “Do I look like something’s wrong?”

“You’re all-” He points at your face, turning his finger in a circle. “Red. Are you getting sick? If you are, you better go home. The last thing anyone needs is the flu.”

“I’m fine.” You reach over and hit the button for the top floor.

“You’re headed to the attic?” He laughs, hollowing out his cheek with a whistle as if to say _glad it’s not me_. “You screw something up?”

“No, I mean, I don’t think so. Why does everyone keep asking me that?”

You know full well that no one of your lowly position gets called up unless they’re on the chopping block.

“I’ve been here a year and I’ve never been above the twentieth floor.” Adjusting his tie Max checks out his reflection in the mirrored wall. “Tell you what, how about I take you out for a drink later? Good or bad, you’re gonna need it.”

“Maybe.” You respond absentmindedly as the elevator dings and Max steps off.

“Good luck.” He gives you a little salute as the doors slide shut and you continue your ascent.

The moment you step off the elevator Pepper is there to give you the third degree en route to Sam’s office.

“If you did something you have to tell me now so that I get in front of it. Everything falls on me. I don’t want to pay the price for your incompetence.”

“I honestly have no idea.” You wish she’d stop talking, you can barely think at the prospect of seeing him again.

“Oh God,” glaring at you she opens the door to his office, gesturing for you enter. “Let me do the talking.”

Sam’s sitting at his desk, fixated on his computer. When he looks up he immediately hones in on you, glancing at Pepper as an afterthought.

“She’s here, finally. I can’t imagine what took so long. I called her twenty minutes ago.”  Lies. “Would you like me to stay?” Pepper asks, grinning unnaturally wide.

“No.” Sam quips. “Shut the door and let me know once everyone else is on the call. I don’t want to be disturbed.”

“Of course.” She turns, sneering silently at you before scampering out of the room.

And before you know it, you’re alone with him again. You don’t say anything, just stand in place as you stare at each other in silence.

“If you want to leave, you should do it now.” He explains calmly, sitting back in his chair. “I won’t stop you and we’ll never speak of it again. But if you stay, you’re giving me consent. Do you understand?

“Yes.” You force out, the fractured word barely audible.

“And what have you decided?” Tilting his head to the side he looks you over from head to toe.

“I’d like to stay.” You’re wet already, squeezing internal muscles and fighting the urge to let your eyes flutter shut.

“Good choice.” His face is expressionless. For being a savant at reading other people he’s just a skilled at cloaking his own emotions. “Come over here.”

Your hands shake as you slowly walk to his desk. He motions for you to come around the side so that you’re standing right next to his chair.

“Do you have a cell phone?”

“Not with me.”

“Bring it with you next time.”

“Okay.”

“Are you wearing underwear?” There’s small tug at the corner of his mouth.

“Yes.” You swallow, closing your eyes for a fleeting second.

“Take them off.” He watches you reach under your skirt and tug the fabric down your legs. Using one hand to balance yourself on the arm of his chair, carefully stepping out of them one high heel at a time. He holds out his hands and you drop them into his palm. “Don’t wear them again.”

_Jesus Christ._

“I won’t.” You confirm. Every inch of skin covered in sweat.

“Sit here.” He taps the end of the desk with two fingers, his eyes never leaving yours. Perching on the edge of the desk you pray you don’t pass out. You can scarcely breathe at the anticipation. “Unbutton your blouse.”

His eyes are relentless, boring holes right through you as shaky fingers pop button after button on your creamy, silk blouse. You pull the material open, giving him a view of the bra underneath. His tongue darts out over his lower lip, his line of sight glued to your tits.

“Pull your bra down, just under your nipples.” He instructs and you comply. A pattern is forming, he has a definite preference for how you display yourself. His eyes dart up from your breasts. “Pull your skirt up and spread your legs so I can see your cunt.”

There’s a split second when you don’t think you can do this, especially not in his office in the middle of the day with a building full of people. But it’s also those facts that turn the fear into excitement, pulsing through your veins.

You stand up long enough to pull your skirt up around your waist, bare pussy on full display as you sit back on the edge of his desk and spread your thighs.

“Lean back and open your legs wider.” He commands as you settle onto your elbows, balancing one leg on the handle of his desk drawer, giving him a pornographic view of your sex. “You’re wet.”

The way he says the words makes it sound like he’s a pious priest and you’re some kind of wanton harlot.

“I like it when you look at me.” You confess, feeling like a whore laid out on his desk with your shirt open and legs spread.

“If you get my desk wet you’re going to clean it with your tongue.”

_Mother Fuck._  You could probably cum just like this. You wouldn’t even need to touch yourself. Just listening to him say shit like that would eventually be enough.

“Mr. Winchester.” Pepper’s voice scared you half to death as she hails him on his intercom. “Everyone’s on the call, they’re waiting for you.”

Sam looks at you, grabbing his cock through his pants. “Stay just like that, don’t move, don’t touch yourself. Just stay open for me. You understand.”

“Yes.” You nod slowly.

Then he picks up the desk phone and hops on a conference call as if this is the most normal thing in the world.

At first, he’s not talking much, just replying with little verbal cues, palming his cock through his pants. He rocks back his office chair, clicking the end of a pen with his thumb and staring at your pussy like the wolf in Little Red Riding Hood. Something on the call sparks his interest because he refocuses on his computer screen, launching into an in-depth explanation about the importance of procedure and process.

Your eyes are closed as you listen to his voice, legs beginning to shake as you keep yourself in the requested position. He’s not doing anything, he hasn’t come close to touching you, at the moment he’s not even looking in your direction, but it’s somehow one of the most sexual and arousing situations you’ve ever been in.

He called you up here to take out your tits, hike up your skirt and present yourself as a piece of erotic art.

The combination of humiliation and arousal has every part of your body on fire. Your nipples are rock hard, throbbing with every beat of your heart, just the same as your clit. You want to close your legs, rub your thighs together to get a small amount of relief. Concentration slipping your legs begin to fall closed and there’s an abrupt, hard smack on the inside of your knee, his open palm slapping your skin.

“Fuck,” you wheeze, mouth falling open.

The mark stings as you stare at him, watching him rub that same hand over his thigh. There’s a red handprint springing to life on your skin, and now it’s throbbing right along with the rest of all your sensitive bits. You tense up, clenching your cunt in desperation. If he had any question about how you’d respond he must know the answer now because you’re twice as wet as before.

He places a hand over the mouthpiece of the phone, “you’re not very good at following the rules.”

“I’m trying.” You whisper. There’s a tear running down your cheek. Perhaps it’s from his hand or maybe you’re just so fucking turned on that your body is responding in unfamiliar ways. More than anything you want him to touch you again, to bring this dormant need to life.

One of your hands leaves the desk and you almost touch yourself, squirming and writhing with little whimpers before you regain control of yourself. When you look at Sam he’s fixed on you like a hawk, eyes narrowing.

“I have to hop off for a few minutes.” He says evenly and hangs up the phone without ever looking away. “You’re not doing very well.”

“I just,” you gulp, unsure of what comes next. “I’m sorry.”

“Look at how wet you are.” He observes casually.

Reaching over he pulls open one of the drawers. Inside there’s a folded shirt and two ties. He pulls out one of the ties, rolling it neatly into a ball. He stands up, looming over you, stepping forward between your legs. “Open your mouth.”

You obey, dropping your jaw open. He firmly stuffs the tie in your mouth, effectively gagging you. You can’t help the desperate moan that gurgles up from your throat.

“Now, stand up and lean over the desk.”

You lock eyes for a moment before you comply, standing on shaky legs and bending forward until your belly is pressed against his weekly calendar.

“Arms up here, hands open, palms down.”

You stretch your arms up, spreading your fingers over the desk. The skirt is still around your waist, ass on full display.

“Spread your legs wider.”

You inch your legs part as far you can. This is a true feeling of utter vulnerability.

“Keep quiet. If you make too much noise someone will hear you.”

And with that, his hand comes down on your right butt cheek with a sickening smack that sends your entire body lurching forward. You’re grateful for the gag as you let out a muffled cry, summoning every ounce of self-control to stay in place.

There are three more in rapid succession, smack smack smack that sends you careening into a whole new world. It hurts, he’s spanking you hard enough his own hand must smart. All you can do is whimper into the gag, dragging your cheek along the hardwood of his desk.

The fifth spank is a quick, nasty slap directly on your bare pussy. It’s not a hard as the ones on your backside, but enough to send a spiral of pleasure and pain twisting up your spine as you groan and lift your head.

“You’re so wet,” his words come out in quick bursts, he’s trying to hold himself together. “This desperate little cunt is drooling.”

He wipes a wet palm over the stinging skin of your ass and repeats his previous set. Four on your ass and one on your pussy. And then he does it again. And one more time after that.

When it’s over you’re sweating and crying, tears of frustration, pain and all-consuming arousal. You’re right on the edge, you just need him to touch you, all it would take is the brush of his fingers and you’d cum like a freight train.

“Puhhh,” you mumble against the gag, fingers clawing the desk.

“You want me to keep going?” He shifts behind you.

“Puhhh,” You can’t get out anything other than unintelligible sounds.

He spanks your pussy again, only this time it’s a lighter touch over your clit. One, two, three little wet whacks that are enough to send you over the edge. You cum, panting with a makeshift gag stuffed in your mouth, bent over his desk, writhing like a bitch in heat.

You’re gasping with a cheek pressed into his notepad when you hear the gentle click of a cell phone camera. It’s followed by several more accompanied by Sam’s satisfied grunt.

“Stand up and turn around.” He commands calmly.

Still breathless, you push yourself up with shaking arms, almost losing your balance as you turn to face him. You rest your butt on the edge of the desk and wince. You’re not going to be able to sit for a week.

Expressionless, he reaches up, pulling the tie out of your mouth with a yank and throws it back into the open drawer as you close a sore jaw.

He carefully, methodically, reaches forward, the warm tips of his fingers brushing the skin of your breasts as he puts your bra back in place. Long nimble fingers button up your shirt, one by one. Then two big hands, pull your skirt back into place. “Come here.”

He places one hand gently on your shoulder, turning you to look into the mirror on the far wall. He’s standing behind you, looming like a giant. Your entire face is beet red, cheeks pink and tear-stained, eyes puffy and swollen. The slick between your legs is wet, cold and uncomfortable but a constant reminder of what just occurred.

Your breath finds an even pace while you stare at each other in the mirror.

“If you want this to continue we’re going to have to set some ground rules. Is this something you’re interested in?” He asks, placing a hand on your shoulder, squeezing as his eyes study the reflection.

“Y-yes.” You can barely speak.

“It won’t ever be anything more than this, just transactional satisfaction. I’ll take what I want when I want it. You understand?”

“Yes.” You respond succinctly.

“Good.” He gives you one final look and steps away. “Sit down.”

He gestures toward the chair across from his desk. You gingerly take a seat, wondering if your ass is going to be black and blue. He scribbles something on a sticky note and hands it to you. It’s an address with no context.

“What is this?” You wipe at your cheeks as you clear your throat, finding composure.

“My personal physician. Be there tomorrow at 2:30. I’ll have an appointment scheduled for you.” He checks his phone, unhappy with whatever he reads and places it screen down on his desk.

“A doctor?”

“I don’t leave anything to chance.” He rests both forearms on his desk. “I don’t fuck with a condom. If you want to take this further, I have certain non-negotiables. I need to know you’re on birth control and that you’re clean.”

You thought you’d reached your capacity for shame but this is a whole new level. You almost choke, clutching both hands together in your lap.

“I-I’m on the pill.” It’s the only viable thought you can manage.

“That’s not good enough for me. You can understand why can’t you?” His fingers strum the files on his desk as he awaits your response.

You understand the logic, all you’d have to do is forget to take a pill or skip it on purpose if you wanted to. There’s the feminist part of your brain that wants to tell him to get fucked. He can’t order you around and assume you’re just going to do everything he wants. But there’s another part, a stronger part, that actually likes the idea of being controlled. It’s not like you can’t say no. You could walk out of this building and never look back. He’d let you go.

But offering your submission is your own version of control. You have to comply in order for this to work. It’s a two way street and you’re the one who gets the final say.

“I understand.” You nod, meeting his stare. “I’ll be there at 2:30.”

“You liked what I just did to you.” He cocks his head to the side. “Was it the pain or the humiliation that got you off?”

You gulp, refusing to look away. “Both.”

“You are  _interesting_.” A smirk crossed his face. “We’re going to enjoy each other.”

“What else is there?  You said you had non-negotiables, was it just the doctor?” You want to know exactly what you’re getting yourself into.

“You can’t ever tell another living soul about what happens between us.” He gets up from his chair and saunters around the desk, sitting on the edge, directly in front of you. “If you want me to stop, you tell me. But once we stop, we won’t continue. Ever. You understand?”

“Yes,” you nod, watching his fingers curl under the edge of the desk.

“You can’t fuck anyone else.”

“Alright.” You agree. The truth is you’d agree to just about anything to have him touch you again. But there is one term of your own that you need to outline. “What about you? If you expect me to let you…”

“Cum inside you?” His finishes, a hint of amusement in his voice as you blush for the hundredth time.

“Yes.” You choke out. “Then I have to be your only partner too.”

“Agreed.” He shrugs with an easy confirmation. You’re not sure its the response you expected but it wasn’t tacit acceptance.

“Good.” You breathe.

“Good.” He mimics, his eyes dropping over your body from head to toe. He leans back and taps the call button on his desk phone. Before you have time to prepare Pepper is bustling into the room.

“Everything alright in here?” She asks coming to stand beside the chair you’re sitting in. She gets a look at your face and forces a smile at Sam. You’re just thankful she can’t see your ass.

“Y/N is going to be working on a special project for me.” He disregards her question, getting up to move back behind his desk.

“Special project?” She looks from you to Sam.

“Confidential.” Sam looks at you, locking eyes and refusing to look away. There’s a now familiar tingle between your legs. “I have an inquiry that I need to keep separate from our other work for proprietary reasons. Y/N has proven her ability to remain discreet. She’ll need access to the executive elevator and an all-hours, unrestricted security pass. I’ll let you know what else as the situation evolves.”

“Of course.” Pepper nods. “Anything else?”

“No. You’re both free to go.” He waves his hands, opening his laptop.

You get up, ready to follow Pepper out of the room but stop for a moment. “Thank you for the opportunity, Mr. Winchester.”

His eyes shoot up from the screen, mouth tightening. “I’m sure you’ll prove yourself.”

With one final look, you walk out of his office. This is surreal, you want to pinch yourself and slap your cheeks just to make sure you’re really awake.

“What the fuck was that?” Pepper hisses the minute the door is closed. “You look like a mess. With all the tears I thought he fired you. You’re lucky, he hates it when people cry.”

“Oh, um,” you stumble, looking for a suitable explanation. “He was…rough.”

“You have no idea.” She rolls her eyes. “What the hell happened at that conference? You said you noted everything and now he’s talking about your ability to be discreet and giving you work.”

“I can’t get into specifics. It’s sensitive.” One thing is clear, he’s never come on to her. She has no idea what’s going on behind closed doors, but that doesn’t surprise you. Sam has a reputation as a ruthless businessman but you’ve never heard so much as a peep about anything scandalous. And to be honest he’s the last person you would expect it from if it hadn’t happened to you.

“Well,” Pepper sighs, hands on hips. “I hope you’re pleased with yourself. God, you have no idea what you’ve gotten yourself into.  He’s a terror to work for, trust me when I tell you that you’re not at all capable of meeting his expectations. You won’t last a week reporting to him.”

“I’m capable of more than you think.” You raise your eyebrows, emboldened by this new situation. Sex notwithstanding, reporting directly to Sam gives you a sliver of power, perhaps just enough that she’ll ease up.

“Just don’t come crying to me when he loses his temper.” She laughs dryly. “I’ll have your new credentials by the end of the day.”

And just like that, your entire life is about to change.

-

**Parts Four and Five** are currently available on [Patreon](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) for a monthly pledge of $2.50. This includes early access to all my stories and Patreon exclusive content.  >> [CLICK HERE](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) << 


	4. Four

A week goes by. You do your very best to act like nothing has changed when inside it feels like gravity has reversed. Up is down and right is wrong. Everything is different.

It’s just after three on Friday afternoon. Everyone is spread thin and that means he has more on his plate than ever. You’ve given up on seeing him alone this week, he canceled his monthly employee engagement meeting twice because of the workload, but it’s been rescheduled for four o'clock today. Two hours and you’ll be out of here for the weekend.

You’ve moved up the food chain, but only marginally. Afternoon mail delivery is now handled by a mousy college freshman named Bea who’s headed in your direction. You’re working to finish the current notes when the squeaking wheel on the mail cart stops at your desk.

“Please don’t tell me there’s more transcription from the Harrison case, I can’t handle any more of Joyce’s shorthand…”

“I don’t have anything interoffice for you - oh wait.” Bea crouches down, pulling a padded envelope from the very bottom of the trolley. “This one’s for you. I don’t know what department it came from.”

“Thanks.” You take it, turning the feather-light package over in your hands.

There’s a small envelope taped to the front that’s stamped confidential in bright red block letters. Ensuring no one else is around you open it, removing the single piece of paper from inside.

_**Open in private.** _

That’s all it says, but the message is handwritten. This is Sam, it has to be.

Taking the envelope you find an available unisex bathroom and lock yourself inside, checking the door twice. Hands shaking, you tear it open and reach inside only to pull out a pair of red panties. Not exactly a thong, but there’s not much to them.

Searching in the envelope you find another note at the bottom.

_**Put these on and come to my office.** _

You haven’t worn underwear to work since your last encounter. He’d probably never know but following his rules makes your everyday a little more exciting. You step into your new gift, pulling them into place and throwing away the evidence before making your way to the rear hallway and the executive elevator.

Pepper is sitting at her desk as you approach, glaring at you with confused hostility. “What are doing here?”

“He asked for me.” You gesture toward the closed door of Sam’s office.

“You’re not on his schedule. The hour before the company meeting is always his prep time. No exceptions.”

“I don’t know what to tell you. He told me to come to his office.” You shrug.

“Well, I don’t have you on the schedule. Who messaged you? There must have been a mix up-”

“He did.” You confirm and she stops what she’s doing to stare you.

“Seriously?” Pepper closes her eyes, shaking her head as if it’s the most ludicrous

thing she’s ever heard. “What the hell does he have you doing for him?”

“I can’t talk about it.” You maintain composure, despite the excitement growing in your belly. He’s right there, on the other side of the wall. You can almost feel him.

“Y/N is here for you.” She announces your presence over the intercom. There’s an immediate reply.

“Send her in. Hold everything. No interruptions.” Sam’s voice commands from the small speaker.

Pepper raises her eyebrows, gesturing toward the door.

Sam’s standing in the middle of his large office, reading from an iPad. He’s rehearsing.

“Hello.” The door clicks shut and you stop where you are, standing place.

“Hello.” He parrots back, removing his glasses and setting them, along with his tablet, on the coffee table.

He appraises you, looking you over, head to toe as his eyes narrow. “You got a haircut.”

“Just a trim.” Your fingers twist into the ends of your hair. “Is that a problem?”

“No, but I would prefer if you start wearing it up when you’re at work.” He studies you thoughtfully. “It can be down, like this, when you’re with me.”

“Okay,” you agree.

“I have one more piece of business we need to get out of the way before we can move forward.” He gestures to the paper on the desk. You move to get a better look, only to find it’s a contract.

“You want me to sign this?” You look at him, unable to hide your surprise.

“Read it, then sign it.” He leans towards you, sliding the paper away from you, almost to the opposite side of the desk.

“Now?”

“Yes.” He takes a step closer, his eyes dropping down to your midsection. “Are you wearing what I sent you?”

“Yes.”

“Good. Now, why don’t you look over the agreement.” He turns you around, big hands curling over your hips until you face the desk.

_Oh._  You get it now.

You have to lean over the desk, your feet nearly leaving the ground, to be able to reach the document. He’s quiet behind you as you pull yourself together enough to read the first paragraph. He wasn’t kidding, this was a legally binding contract that started with an explanation of how any and all conversations and interactions between the two parties are to be kept confidential.

There are two hands on the outside of your legs, sliding under the hem of your skirt. You suck in a breath, fingers curling against the desk as he begins to lift the material up. “Do you have any questions?”

“I-I um,” you skim the rest of the paper. It’s basically a gag order, you tell anyone about this little arrangement and Sam can ruin your life. “This is what we talked about before.”

“Yes.” He purrs, successfully pulling your skirt up over your round little ass. The pads of his fingers trail along the edge of your panties. “Sign it.”

You pick up a pen off the desk and scribble your name at the bottom without a second thought.

“You’re good at taking orders today.” One of his hands grabs the globe of your ass, kneading the flesh. “Stand up and undress, everything except these.” He gives you a pat on the ass and you stand up, turning to find him watching you intently.

While he’s seen the most intimate parts of your body, he’s never seen you naked before. You have to look away from his eyes as you pull your sweater off, then unzip your skirt and step out of it. Willing a steady hand you reach behind your back, unhooking your bra and letting it fall to the ground.

His office is cold and your nipples are rock hard within seconds as you stand there, practically naked, on display. “Would my like me to keep my heels on?”

“What did I say?” His eyes tick up from your breast to give you an annoyed tip of his head.

“Right,” you whisper, slipping off your pumps, toes curling into the plush carpet of his office.

“Turn around.” He twirls his finger in the air.

Slowly, you rotate in a small circle, letting him have a view of your body from every angle before facing him head-on.

“You have a beautiful body.” He comments matter-of-factly.

“Thank you.” Your response is barely audible.

Every time you’re with him, his very presence elicits anxious arousal that’s wholly unique. Despite his demeanor, he makes you feel more wanted than any man you’ve ever been with.

“Tell me, Y/N. Do you like sucking cock?” A grin tugs at his mouth, one hand shoved in his pocket.

Your entire body goes hot, quaking excitement sparks in your veins. This can go one of two ways, you can melt into a puddle on his expensive carpeting or you can pull yourself together and act as if you’ve actually seen a penis before.

You find your voice, lifting your chin.

“Yes, I love it.” You lock eyes with him.

“We’re about to see just how much you love it.” His tongue darts out, licking his bottom lip. “Over here, on your knees.”

Walking to him you get close enough to smell his aftershave, staring up at him for a second before dutifully dropping down, kneeling at his feet. You reach for his belt, but think better of it. “Should I?”

“Stay just like you are until I tell you to move.” He reaches down, trailing his thumb lightly over your cheek before unbuckling his belt, the subtle sounds of leather sliding against metal are all you can hear.

He unzips himself, suit pants dropping to his thighs, revealing plain boxer briefs underneath and the massive bulge of his cock. He palms his erection through his underwear and you watch, spellbound by the sheer size of him.

“Do you want it?” He asks evenly. You wait a moment, before you look upward to find him staring down at you, eyes glazed with lust.

“Yes,” your pussy is soaked, aching between your thighs.

“Beg me for it.”

You whimper, looking from his face to his hand rubbing his dick.

“Please let me suck your cock.” It’s forced this first time, you’ve never actually asked to give a blow job before. But Sam is all about firsts, it’s his specialty. The moment the words leave your mouth, there’s a throb growing stronger, your empty cunt clenching in anticipation.

“You can do better than that.” He shakes his head.

“Please,” you sit up a little, looking up at him and giving in to your own need. You do want it and you only have to tell him to get what you want. “Please, I want your cock in my mouth. I wanna choke on you, take you in my throat. Please let me suck your cock.”

“That’s better.” He spits, shoving his boxers out of the way as his dick springs upward, bobbing in front of your face. “Open up.”

You don’t wait, just wrap your lips around the swollen head of his cock, sucking as if your life depends on it. He grunts and you take it as a sign of approval, sliding your tongue along the underside of his shaft. He’s huge, thicker than any man you’ve encountered before. You’d guessed from his stature that he was well endowed but this is something else altogether.

Cupping his balls in one hand and gripping the base of his length with the other, you begin to bob up and down, taking more and more with each pass. It’s not long before he’s tapping the back of your throat. Now it’s time to show him just how much you really want this.

Taking a breath you prepare yourself for the burn, letting him slide as far down your throat as you can bear. You hold him there, letting the muscles of your throat flutter around his cock before pulling back to take a breath as spit drips down your chin. Two lungfuls of air and you’re right back at it, bobbing like before only letting him slide deep with each stroke.

You feel a hand on your hair, twisting his fingers into your locks to get a tight grip. He pulls you back, painfully yanking on your scalp.

“Deep breath.” He instructs as you gasp like you’re about to dive underwater. He pushes you back onto his cock, shoving his hips forward and lodging himself right back in your throat, holding you there. His free hand reaches down, rubbing over the bulge of his cock in your throat. “Relax. Breathe through your nose and relax.”

You manage another two inches, gurgling on his cock, drool running down your chin, eyes watering before he finally releases you.

“I can do better.” You sputter, wiping your mouth, looking up at him. “I can take it all.”

“Ambitious.” He grins, a first genuine expression you’ve seen so far.

“Please, help me.” The words  _help me_ trigger something in him, his eyes narrow, mouth tightening.

“You’re gonna to stay still while I fuck your mouth, you understand?”

“Yes.” You nod, dropping your jaw open and sticking out your tongue. If you didn’t feel a whore before there’s no escaping it now. It’s a feeling that you didn’t know you craved, didn’t know you needed so badly, until he came along.

He grabs a handful of hair in each hand and forces his cock back into your waiting mouth, punching his hips forward at a comfortable pace. Every third or fourth stroke he pushes deeper and deeper until every thrust is testing your limits. And right when you think you can’t take anymore, he pulls you forward, pressing with unrelenting force as you fight the gag and your nose presses into his neatly trimmed pubic hair.

He rewards your efforts by pulling back for a moment before repeating the thrust. Then he does it again and again until your face meets the skin above his cock with every thrust. His soft grunts are closer and closer together. You wonder if he’ll cum right down your throat, but just as he’s nearing his peak he yanks your head away, leaving you gasping, mouth open and eyes watering.

“Up,” he uses his grip on your hair to lift you off the ground, backing you up until he can reach behind your hips to brace his hands on the desk.

He pulls your panties down around your thighs, bending his knees as he jerks himself. The tip of his cock is between your legs, an inch away from your dripping pussy and all you can think about is how badly you wish he’d turn you over and slide inside-

He cums with a muted groan, pressing the head of his dick into the crotch of your panties, shooting pearly ropes of cum until his spunk is thoroughly coating the red lace.

You’re panting, chin still wet from sucking his cock as you look down at his seed pooled in your underwear. He leans over, plucking a tissue and wiping the tip of his cock before tucking himself back inside his boxers.

You’re frozen as he reaches down and pulls ruined lace back into place, allowing you to feel the obscene wetness of his load pressed against your aching pussy. He pats your cunt twice as if to say _job well done_ before hiking his pants back up.

“Get dressed.” He doesn’t even look at you, tucking his shirt back in. “If you make it through the meeting without squirming too much, I’ll let you cum once it’s over.”

You can’t speak. Sam goes back to reviewing his notes without another word and you wander into the bathroom, taking stock of yourself in the mirror. After several minutes of dabbing at your makeup and smoothing your hair back, you manage to look somewhat presentable but all you can think about is the thick mess between your legs.

When you emerge from the bathroom he’s adjusting his glasses in the mirror, glancing up to appraise his handiwork.

“Should I go?” You ask, squeezing your legs together.

“No. You’ll stay with me,” he instructs as there’s a knock on his office door. “Come in.”

“It’s time. You have to leave now if you want to be on time.” Pepper steps inside.

“I’m ready.” He confirms, looking to you as he heads out. “Lets go.”

“Where do you think you’re doing?” Pepper tries to stop you as you follow Sam out the door.

“I need her.”  He offers with even looking back.

Sam leads the way, walking a breakneck pace as you and Pepper jog behind him.

-

The auditorium is on the other side of the sprawling campus. This once small law firm has erupted into a multifaceted company specializing in the tech industry, dealing in everything from intellectual property rights to a division known as The Institute that assists in writing policy for political approval.

All of this is Sam’s brainchild.

The monthly meeting is less a traditional meeting and more a presentation. A thousand employees pack into the auditorium to listen to Sam talk about the future of the company, where they’re headed and how each person is a integral piece of the puzzle. He’s an engaging speaker, his success speaks for itself, but seeing him on stage is whole other animal. He’s given three TED Talks, each one racking up millions of hits on Youtube.

Other members of the board of directors are often on stage, sitting in chairs, watching and nodding in approval. Pepper is always directly behind him, arms folded into her lap, transfixed or at least faking it.

Someone from IT is hooking a mic pack onto the back of Sam’s suit pants as Pepper goes over the last minute changes. It’s a few more minutes of prep and then he’s ready to address the company. You look around, unsure if you’re meant to stay backstage or find a seat in the audience with everyone else, when Sam turns back to you, cocking an eyebrow.

“What are you doing?” He snaps his fingers. “Come on.”

“My God.” Pepper hisses, grabbing you by the arm and pulling you with her.  

By the time you walk out onto the stage there’s a smattering of applause rising from the audience. An extra seat is placed next to Pepper’s chair and you sit down as Sam begins to speak.

The employees here are engaged. It’s a progressive company that offers competitive benefits and obscene salaries for anyone who’s willing to work hard and put in the hours. Sam’s a son of a bitch and a tough guy to work for, but he puts his money where his mouth his.

There are two spotlights above the stage shining down onto you, hot as the noon time sun. After five minutes you’re sweating, and after twenty it takes everything you’ve got to stay still in your seat.  For an hour you do your best to just sit there in front of a thousand people, with Sam’s cum wet and warm between your legs.

Just when you think you can’t take anymore, there’s a round of applause and you realize he’s done. You jump up to follow him, happy to be out of the public view. He stops in the wings, turning to Pepper.

“Wait here.” He instructs. “Y/N, with me.”

There’s a small, windowless room to the right of the stage. It’s big enough for a table, two chairs and not much else. Sam shuts the door behind you, reaching for a lock but there is none. There are crystal clear voices just outside the room, there’s no privacy in here.

“Stand here.” He points and you comply, walking toward him, resting your back against the unlocked door. He pulls your skirt up, snaking his hand underneath, wedging between the sticky flesh of your thighs. “Were you paying attention out there?”

His voice is low, just loud enough for you to hear.

“No.” You murmur as his fingers slip inside your panties, pressing over the mound of your sex, then lower. “I was so hot I-I couldn’t pay attention.”

“Is that why?” He smirks, stepping closer. He’s sweating, just the same as you, body heat radiating off him. “Next time I expect you to take notes. There’ll be a quiz afterward.”

“I’ll do better.” You nod, mouth falling open.

“You have homework this weekend.” His eyes are relentless, he’s so close you can feel his breath on your cheek. His fingers are playing over your sex, the tips just barely pushing between the lips of your pussy.

“I’m a good student.” You mean it honestly and his eyes narrow, looking at your mouth with a carnal hunger that you’re getting to know well.

“Every morning, and every night, I want you touch yourself. Make yourself wet but don’t cum. No orgasms until the next time I see you. Understood?”

“Understood.” You swallow, your pussy throbbing, begging for him to slide inside and offer relief.

“You did well today.” He cooes, leaning forward, pressing the weight of his body against you, pinning you to the door. “You’re a mess down here. Did this turn you on? Feeling my cum between your legs with everyone watching?”

“Yes.” You whimper, legs shivering.

“Do you want me to make you cum now?” His mouth is against your ear, the heat of his body nearly suffocating. He’s big and heavy, you couldn’t move if you wanted to.

“Yes, please.” Panting you try to open your legs further. You want him to shove his fingers inside you, to bend you over and fuck you so hard you won’t be able to walk.

“No more talking.” He hisses. “Don’t make a sound.”

His middle finger dips into your cunt, but only enough to wet the tip before finding your clit. He rubs you firm and even,  _up and down, up and down_ over your throbbing apex as you struggle to suppress the urge to moan. It doesn’t take much, maybe a minute of his finger working diligently until your orgasm builds and explodes. He clamps his free hand over your mouth, the weight of him pushing the breath right of your lungs while you whimper into the palm of his hand, empty cunt clenching again and again.

He removes his finger from your clit, cupping your pussy with his whole hand between your legs, gasping in his hand as he keeps you in place, silent and struggling to stay upright. If he weren’t supporting your weight, you’d already be on the floor.

“Say t _hank you_.” He whispers, taking his hand away from your mouth, placing it on the wall beside your head. Pulling back he looks at you, that intense gaze that gets you every time. The hand cupping over your sensitive cunt gives a gentle squeeze and you flinch in response.

“T-Thank you.” You mutter, throat bobbing, swallowing hard.

“You’re welcome.” He steps back, relieving you of his hands and body as you nearly wilt to the floor, barely managing to stay upright. He takes a moment, smoothing out his shirt, adjusting his tie before giving you a final look and then he’s gone.

-

**_Part Five & Six _**are currently available   on [Patreon](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) for a monthly pledge of $2.50. This includes early access to all my stories and Patreon exclusive content.  >> [CLICK HERE](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) << 


	5. Five

That Friday night, after a quick run and pre-packaged dinner you settle in for a quiet night at home. If you go out, it’s always on a Saturday, Fridays are typically reserved for decompression, a little self-care, and Netflix.

It’s almost midnight when you finally shut off the TV, but don’t move off the couch. Sam’s homework has been on your mind since you left, dazed and confused, earlier that afternoon.

It’s an interesting prospect, the idea that his control reaches outside of your in-person meetings. He wants to work his way into your everyday routine, little reminders of his ability to get you to follow orders. You don’t _have to_  do anything, he’d probably never know the difference. He’s only able to exert as much control as you’re willing to give up and you can recognize the power in that.

But there is something appealing about the idea of giving these pieces of yourself to him. There’s something about the concept of obeying orders that appeals to a part of your desires that are suddenly alive and vying for control.

Lying back on the couch you snake a hand inside your pajama pants, rubbing your clit, remembering how it felt when he was touching you. It doesn’t take long, just a few minutes of letting your mind wander and fingers stoke. It’s not long before all too familiar need blossoms between your legs. Dipping a finger into your pussy you’re not all surprised at how wet you are. It feels like you’ve been in a state of arousal since your first encounter, neediness that grows with each passing day.

Using your own slick you go back to touching yourself, bringing your body right to the edge before removing your hand. You give yourself a minute, allowing your body to calm down and then resume the touch, edging yourself again. And then again. You almost cum, it’s a close call but right before you’re about to tip over that edge you pull your hand away, legs clenched together, teeth sunk into your bottom lip.

That night you lay in bed in frustration, pussy aching with no relief in sight. You don’t touch yourself again until the following morning when you complete the task again, edging twice before getting up for the day. By the time the weekend is over you’re a desperate mess ready to do just about anything to find relief.

-

Monday becomes Tuesday and there’s still no word from Sam. Attempting to focus on work is a task in and of itself because you’re living in constant anticipation of what his next move might be.

“Hey, you.” Max is suddenly in your cubicle, sitting on the edge of the desk.

“Hi,” you smile, glad for any and all distractions. “Long time, no see.”

“I’ve been working on the Jablonski case. A bunch of us got sent to Orlando for depositions.” He shrugs like it’s no big deal, but in truth, he loves to peacock. “Trina told me you’re working on some hush-hush project with Sam. What the hell does he have you working on?”

He’s teasing but he also wants the details. Max is always in everyone’s business, it’s how he got to where he is. He uses any and all information to his advantage. The last thing you need is him sniffing around.

“I can’t talk about it.” You mime zipping your lips with your fingers.

“Oh, come on,” he places a hand over his heart. “It’s me. Give me a hint.”

“I can’t.” You nod succinctly.

“Did you hear he chewed Lacy a new one? I don’t know what she did but Pepper said she was hysterical after she left his office. Didn’t stop crying for an hour. He’s got a real way with people.”

“He’s got high expectations.” You shrug, squeezing your thighs together at thought of your dirty little secret.

“You must have figured out how to work with him. He doesn’t tolerate any of us lowly plebs.” He grins, leaning closer. “Come on, give me a hint.”

“Nope.”

“I’ll get it outta you.” He grins.

Max is all charm. There was a time when you entertained the idea of hooking up with him but those days are long since past. The idea that anyone will ever make you feel as exhilarated as Sam is laughable.

“No, you won’t.” You tap the desk, spinning the chair back toward the computer. “I really need to finish this.”

“What you really need to do is wrap up for the day. Let’s go to Lucky’s and have a drink, I still owe you one.”

Sighing, you look at his lopsided smile. “I don’t think that’s a good idea.”

“Why not? I don’t bite, too hard.” He’s grinning like a wolf.

“Number one,” You raise a finger. “I don’t date people I work with. Number two, I’m kinda seeing someone.”

“Well, as luck would have it, I’m not trying to sleep with you.” He makes the sign of a cross over his heart. “And frankly my feelings are hurt that you think I have such salacious motives. I’m nothing if not a gentleman.”

“Alright,” you roll your eyes. “Enough with the choir boy routine.”

“One drink, no ulterior motives. We’re friends, that’s all.” He offers.

The truth is you don’t have many friends, certainly no one at work. It would be nice to make an actual connection.

“One  drink, nothing else.” You warn.

“I swear.”

-

By Thursday you’re sure Sam’s homework is designed to kill you. You’ve almost given in half a dozen times, desperate for orgasm but somehow summoning enough resolve to not indulge. But you’re not sure how much longer you can keep it up.

Your phone vibrates in your purse and you retrieve it, looking at a text message from an unknown number.

_**Come to my office. Bring your phone.** _

You nearly jump out of your seat, phone in hand as you jog to the elevators. Every time you’ve been with him it’s a different experience and today will no doubt be something new.

Pepper’s desk is empty and the door to Sam’s office is open. You approach, listening to Sam’s voice as you pop your head in the door with a gentle knock on the doorframe. Sam’s on the phone, but looks up, motioning for you to come inside. Pepper is taking notes, glaring at you from her seat.

“That’s fine - I just don’t want to get caught up in something we’re not prepared for - I understand - That’s no problem - I’ll see you next week - you too.”

He turns to Pepper. “Set up a meeting with him next week. It needs to be in-person, so if he can’t come to me I’ll need the necessary arrangements to go to California.”

“Of course,” Pepper nods. “The finance team needs five minutes later this afternoon. Devin wants final approval of several projects before he starts allocating specific budgets.”

“Whatever he needs.” Sam looks to you, his tongue darting out over his lower lip. “Are you free right now, Y/N?”

“Of course.” You offer, afraid to speak to him in front of anyone else. It feels like this secret might tumble out without warning.

“Wonderful.” He quips, plucking his suit jacket from the back of the chair. “I’ll be back in an hour.”

You follow as he walks out of the office, never exactly sure of what he expects. Standing next to him on the elevator you’re silent as the door slides closed.

“How are you?” He asks, looking forward.

“Frustrated.” You answer honestly.

“Sounds like you completed the tasks I gave you.” The comment sounds off-handed as if he’s talking about the weather while he adjusts his watch.

“I did.” The floors tick by as you descend. “It was…challenging.”

“I wouldn’t have picked you for my special project if I didn’t think you weren’t up for a challenge.” He turns toward you, looking you over in approval. “Besides, that was just the beginning. We’re going to test all kinds of limits.”

The elevator dings and you follow him out into the lobby of the main building. People part like the Red Sea, watching him as he strides toward the doors.

“Where are we going?”

“There.” He points across the campus to the new construction.

The company is growing at a exponential rate. There’s always renovation or new buildings popping up. This building is much smaller than the one you currently work in, it looks to be four or five stories. “Who’s going to work here?”

“IT,” Sam replies, climbing the stairs as you bound behind him.

There’s a construction team breaking for lunch,  men sitting on the floor eating sandwiches and McDonald’s. The foreman makes his way over to Sam, blueprints in hand.

“Mr. Winchester!” He smiles.

“How’s progress?” Sam shakes his hand, looking around the naked room, electric wires hanging from the gutted ceiling.

“Right on schedule.” The foreman glances at you before showing Sam the new set of schematics. After several minutes Sam signs off on the upcoming work. “The top floor is finished?”

“Last week.  I sent your assistant,” he hesitates to look at you. “Your other assistant, the photos. The keycard should work, go check it out.”

“I think we will.” Sam nods.

–

Sam slides his keycard at the glass doors and they open automatically. There are rows and rows of computers in a bright open space with smaller offices off each side of the room.

“The rest of the building should be ready by the end of the month.” He explains, not bothering to turn on the overhead lights. He wanders off toward the back and you follow him into a brightly decorated breakroom. Complete with unused ping pong table and big screen TV. “I thought about moving my office, but I like my current view.”

He turns back to look at you, taking a seat on a small couch next to the coffee machine.

“It’s nice.” It’s hard to make small talk, not when all you can think about is whether he’ll put his hands on you again. “Why did you bring me here?”

“I wanted to get out of my office.” He shrugs, palm ghosting over the crotch of his pants. “Take your clothes off.”

_Here we go._

You strip on command, shedding your clothes until you’re completely naked, standing in front of him with arms at your sides.

“You wore your hair up.” He smiles approvingly.

“Everyday, since you asked me to. Would you like me to take it down?”

He bows his head in confirmation. You pull out the pins holding the bun in place, letting hair fall around your shoulders.

“How many times did you masturbate between the last time you were with me and today?” Sam has a way of asking this kind of filthy question like he wants to know what you’re having for lunch.

“Every morning and night, just like you told me to.”

“Did you let yourself cum?”

“No.”

“What did you think about when you touched yourself?” His head tilts to the side, staring at your tits. You blush, looking at the floor and he corrects you instantly. “Look  _at me_  when I’m asking a question.”

You snap to attention, a familiar tingle blooming between your legs.

“I thought about the way you touch me, how you talk to me.” You have to shift your weight from one foot to the other, feeling vulnerable on multiple levels. “All the things I want you to do to me.”

“What kinds of things?” His fingers playing over his belt buckle, eyes never leaving you.

“I want you to touch me, fuck me, cum on me.” You force yourself to confess more. “I liked it when you spanked me. I’ve never experienced pain and sex before. It makes me wonder what else I’d like.”

“We’re going to find out.” His eyes hone in on you, curling a finger for you to come to him. He sits up as you stand in front of him. His hand slides between your legs, slapping your thighs apart. “Wider.”

You adjust your stance, as he reaches between your legs, pressing his thumb over your clit. At the pressure your eyes roll back into your head, a whimper escaping.

His thumb continues to rub, while his middle and index finger slide along your slit, pushing in with just the tips. “What do you want most right now?”

“Something inside of me.” You whimper, hands clenching at your sides.

“When you were touching yourself, did you fill up your cunt?”

“Yes,” You nod. His fingers are stroking lightly over your sex.

“What did you use? Your fingers?” He looks up at you, awaiting a response.

“Yes…and…a vibrator.” You manage to choke out.

“From now on, nothing goes in your pussy unless it’s my fingers or my cock. Understood?”

“Yes,” you nod, teeth sinking into your lower lip.

His hand leaves your body, and you open your eyes, looking down at him. He gets one glance at the desperation on your face and chuckles as he undoes his belt.

“I’m going to let you use my cock.” He explains, sliding his slacks down, then his underwear as his thick cock springs upward, curved toward his stomach. “No fucking, just rub your pussy on me until you cum.”

You’re excited and ashamed but ready to do almost anything to get some relief. “Okay.”

He grabs your hips as you straddle his lap. You have to watch to line yourself up, trapping his cock between your crotch and his stomach. You slide your pussy along the underside of his shaft as you roll your hips up and down, coating his length in slick. The feeling of anything other than your own fingers almost does you in with one pass. The swollen crown of his cock catches under the hood of your clit and you let it press back and forth, up and down against the V under the head of his dick before going back to the long strokes, letting the length of him slide between the dripping lips of your cunt.

In no time he’s coated in your arousal, allowing you to easily slide over him, your clit throbbing, aching at the constant drag. It takes every ounce of self-restraint not to mount him and sink down on his dick.

“I’m gonna cum.” You rasp, bracing as your fingers curl into the thick muscle of his shoulders.

“Go ahead.” He grunts, watching intently as you rub yourself up and down his cock.

Pleasure racks every inch of your body with the most intense orgasm you’ve ever felt in your life. All those early mornings and late nights teasing yourself, culminate in this one burst of pleasure that has you shaking from the force of the release. You can’t help the moan that erupts from your throat as you cum so hard you can barely see straight. When it’s finally over you slump forward, resting your forehead on his shoulder, pussy twitching and pulsing against his erection.

“Thank you.” You whisper and he pats your ass cheek in response.

“You deserve it.” He pushes you back, looking you in the eyes. Both his hands cup your jaw, it’s a gentle touch that’s out of character, but his words make up for it. “Now, get on your knees and suck my cock like a whore.”

You blink, empty cunt clenching at the word  _whore_ , your body reacting despite the fact that you’ve just had an earth-shattering orgasm. Slithering off his lap you drop down to your knees between his legs and quickly take him into your mouth.

You can taste yourself as his hand twists into your hair, lifting you up and down on his cock. The first few minutes are just a warm up as you get used to the size of him, taking him further and further into your throat with every pump of your mouth.

When his patience runs thin he takes matters into his own hands, holding your head in place while he fucks up into your mouth for the better part of twenty minutes. When he gets close he holds you down, forcing you to take every inch before finally easing up, letting you suck him at your own pace.

He cums, spurting thick and warm. You swallow immediately, letting him fill your mouth a second time before he’s done cumming. Then continue sucking the head of his cock until he grabs your hair and pulls you off his dick.

“Did you swallow it all?” He asks, watching spit drip from your chin.

“Yes.” You gasp.

His thumb hooks over your bottom lip, pulling your jaw open. “Let me see.”

Opening wide for inspection, you feel his thumb rub over your tongue, sliding into the back of your mouth before releasing you.

“Next time I cum in your mouth I want you to hold it, don’t swallow until I tell you.” His knuckles slide over your cheek.

“Okay.” You whisper. “I will.”

“I know.” He tucks himself back into his pants. “Tomorrow I want you here by six thirty am. I’ll text you instructions in the morning.”

-

It’s on the walk back to the main building that you remember his request. “You asked me to bring my phone.”

“I did, thank you for reminding me.” He holds out his hand for your iPhone. “What’s your pin?”

“Um,” you hesitate but answer before you think better of it. “Twenty-two, fifty-two, eighteen.”

He thumbs in your code and unlocks the screen, opening your text messages.

“Hey!” You protest, reaching toward him. He jerks his hands away, shooting you a look of utter intolerance, raising his eyebrow until you slink back, unhappily crossing your arms. You stand watching as he skims your messages, then opens the thread from the unknown number he texted you from earlier. Opening the contacts he inserts a name before handing it back to you.

“Keith Campbell.” You read. “You can’t just check my phone, go through my personal things.”

“I just did.” He looks at you, glancing up to nod at a passing employee. “Don’t worry, I have no interest in monitoring your texts. As long as you’re sticking our agreement.”

“I am.” You confirm.

“Then pull yourself together. We’re going to have a big day tomorrow.”

-

**_Parts Six and Seven are_**  currently available on [Patreon](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) for a monthly pledge of $2.50. This includes early access to all my stories and Patreon exclusive content.  >> [CLICK HERE](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) << 


	6. Six

You hardly sleep. The anticipation of knowing that you’re going to see him early Friday morning is enough to make you vibrate with nervous, jittery energy like a hummingbird in flight. Figuring you might as well use this newfound exhilaration to your advantage, you spend most of the night cleaning your apartment until the bathroom and kitchen are sparkling. It’s well past midnight when you finally crawl into bed, lying there, staring at the ceiling and wondering what new experiences tomorrow will bring.

-

The clock ticks six-thirty but you’ve already been at your desk for half an hour. With the exception of the security team the place is a ghost town. The ding of your phone echoes in the silence as you nearly jump out of your skin.

_**Keith Campbell:**  Come to my office._

You’re up and out of your seat in a heartbeat, hightailing it to the executive elevators. The door to his office is wide open, and you step inside, sunlight pouring in through the floor to ceiling windows. Sam is seated on the sofa in the middle of the room. He looks up, seemingly pleased with your promptness.

“Close the door.” He instructs as you turn back. “How are you this morning?”

“I’m,” you stop to look at him, hair carefully tucked behind his ears. “A little tired.”

“Didn’t you sleep well?” He raises an eyebrow in question.

“No, I was…excited for today.”

“Let’s hope it lives up to expectations. Come, sit there.” He points to the armchair across from the couch. You take a seat, crossing both ankles, clasping your hands in your lap. He watches every movement, eyes flitting to each part of your body, taking stock.“You will spend the entire day with me. That entails meetings, the business review, all of it. When we’re in a room with other people, you’ll stand or sit next to me, clear so far?”

“Yes.” You nod.

“I’ll give you a laptop, you can take notes, something to make yourself look useful. Now, and this is the most important part, you’re not to talk to anyone other than me. If someone speaks to you, defer to me. Can you do that?”

“I can.” Your mind is already racing with a hundred different uncomfortable scenarios but then there’s an undeniable thrill at the idea of complying with this instruction. “I won’t speak to anyone but you.”

“Excellent. Shall we get started?” His eyes narrow and you know the day will be much more than note taking and structured silence.

“I’m ready.”

“Sit back, spread your legs and touch yourself. No orgasm.”

_Oh, God._  You wordlessly pull your skirt up and open your thighs, snaking a hand between them. Sam watches for a moment, emotionless, and then picks up his newspapers and goes back to reading. There’s the instant conflicted mix of embarrassment and arousal as you rub your clit while Sam sits across from you, going about his morning as if you’re not even in the room.

You’ve been wet since you woke up, every inch of you alive at the thought of what the day would bring. So it’s no surprise that it doesn’t take long to get close, cunt clenching as you hold your own pleasure at bay. A moan escapes your lips, small and barely audible but he hones in on it like a hawk.

Glancing up he clears his throat, watching your rub yourself, stopping every third or fourth stroke to keep from cumming.

“I don’t like labeling things,” He goes back to his paper, as if engaging in casual conversation. “I won’t ever tell you that you have rules because all this is your choice. What I do have are expectations. I’ve already outlined several of them. Can you tell me what they are?”

“Oh god.” You groan, slowing your fingers to a glacial pace. “No panties.”

“That’s one.”

“No talking about us.”

“I would say that’s more of a technicality but I’ll give it to you.”

Your mind races over your meeting with him yesterday, gasping and dipping your fingers down to wet them with your slick before returning to your clit. “Nothing inside my pussy except your fingers or your cock.”

“You were listening.” He grins, folding the paper over his lap. “Tell me, is that something you want? To have me inside you?”

“Yes.” You stare at him head on, legs beginning to shake.

“We’ll see how well you do today.” Taking off his glasses he leans forward, getting a better view of your cunt. “Why don’t I tell you what I have in mind.”

You nod, unable to form words, neck snapping back against the chair.

“Don’t stop touching yourself, just slow down and control your body. If you cum without permission, you’re not going to like the repercussions.”

“I won’t.” You’re determined to show him you can take as much as he can dish out.  

“After your first time in my office, when I spanked you, did it hurt afterward?”

“A little,” you lock eyes with him. “At first I assumed I’d have bruises but it was just red and that went away pretty fast.”

“Did you like the way it felt?”

“I loved it.”

“You’re going to be doing a lot of sitting today, there are more meetings than usual. So I’m going to spank you so hard you’re gonna feel it until Monday. When I’m done spanking you, I’m going to put a plug in your ass. That tight little bottom is going to be sore, and full, until you leave at the end of the day. If you’re good and do everything I tell you, I’ll let you fuck your pussy with my fingers.”

“Thank you, I want that.” You reply with a sharp breath and Sam’s eyes light up.

You hoped he’d spank you again. It’s been on your mind since that first time, but there’s always another level with him, that’s what really crawls under your skin. You’ve had anal sex a handful of times, none of it was particularly pleasurable for you, but it’s something you’ll try if he wants. The truth is you’ll do just about anything he asks of you.

“Get up, come over here and lay across my lap.” He sets the newspaper on the coffee table as you stand up and walk to him, sticky thighs rubbing together as you move.

Hiking up your skirt you crawl over him, lowering your weight so your belly is over his crotch. He’s hard, you can feel that huge cock straining through his suit pants while you wiggle your ass in the air.

“You count.” His thumb dips down between your legs, checking to see how wet you are before wiping it on the back of your thigh. He grabs a fist full of your butt cheek with one big, warm hand, giving it a squeeze as his palm comes down on the opposite cheek.

_Crack._

You wince. This first one is harder than anything he did before but the pain instantly blooms into pleasure, skin stinging from his hand.

“One.” You count, voice already shaking.

_Crack. Crack._

These two are on the same cheek, two hits in rapid succession in exactly the same spot that makes you see stars, sucking deep breathes.

“Three.”

_Crack._

This is the hardest yet, on your virgin cheek and you squeal, a high pitch yelp that turns into a groan.

“Four.” You’re sweating, fingers curling into the fabric of the sofa.

“Deep breath,” he warns, voice low and even, with his hand rubbing the burning skin. You suck in a breath and then he really gets started.

_Crack. Crack. Crack. Crack. Crack._

They’re ungodly hard and incredibly fast, alternating between cheeks until you can feel the tears pool at the corners of your eyes.

“Eight.” You whimper.

“Wrong.” He corrects you immediately. “That was nine.”

_Crack. Crack. Crack. Crack._

Again the spanks come in rapidfire succession, hard enough to draw a bark with each one.

“Th-thirteen.” You sputter, tears now falling freely. “It hurts.”

“Good.” He quips. His hand moves between your legs, searching until he finds your clit, rubbing it with his thumb. After a few well placed strokes, his free hand comes down your ass again.

_Crack._

“Do we need to stop?” His inquiry is accompanied by an increasing pressure over your aching clit.

“No,” you nod adamantly. “I can take more. I wanna feel it later.”

“You don’t disappoint, do you.” He smirks.

He alternates between rubbing your clit and spanking your backside until you’re squirming on his lap, barely able to lie still. Your butt hurts so bad you feel your heartbeat, the flesh throbbing like a frayed nerve, but he’s got you right on the edge. If he’d just rub you a little bit longer you’d cum in an instant.

Crack.

“Thirty.” You cry out, slapping a hand over your own mouth to contain the sob.

Sam places a hand on the back of your thigh, right under your buttocks as his thumbs stills over your clit.

“You should see your ass, you’ll be thinking about me all weekend.” There’s a smirk in his voice, as he leans over, pressing a hand on your lower back to keep you in place. Then the click of a bottle and he’s rubbing lotion over your cheeks, big hands massaging the tender flesh. Under any other circumstances, it would feel good, but right now it just stings like a mother fucker. “Are you ready for the next part?”

“Yes.” You confirm with the side of your face smashed into the couch cushion.

“Just relax.” There’s the click of another bottle opening but you don’t feel anything until he’s pulling your ass cheeks apart. Then the wet, cold press of lubed metal as he presses something against your tight hole. “Don’t worry, it’s small, just enough to make you feel it….that’s it, open up for me…”

It’s a firm press, agonizingly slow as the plug stretches you open, wider and wider until the flared end slides inside with a quick burn and then your body is closing around it.

“Oh,” you mewl at this new, not unpleasant, sensation.

“You should see yourself.” He’s got both hands back on your bruised ass, pushing your cheeks together and then pulling them apart. “You’re all marked up. And your pussy is so wet you’re going to make a mess of this pretty skirt. Better clean you up.”

He plucks a Kleenex from the side table and wipes up and down your slit until you’re no longer sopping wet.

“Get up.” He pats the couch between your legs.

You slide off his lap, settling onto your knees on the couch, sitting back, wincing as your butt meets your heels.

He looks over your face for a moment before reaching up to wipe your tears away with his thumb. “You’re beautiful like this. Desperate, frustrated, embarrassed. It’s fucking perfect…do you like how this feels? Was it too much?”

“Wasn’t too much.” You’re aching, everything between your legs is begging for release. You have no idea how you’re going to make it through the day.

“We’re not done yet.” He glances at his watch. “But we do need to hurry. Pepper will be here soon. You’re going to suck my cock now.”

“Okay.” You agree eagerly, watching him unbuckle his belt. You’re so turned on, the idea of having him in your mouth is almost as appealing as him fucking you.

The moment his cock springs free you curl your fingers around him, leaning down to suck on the swollen crown and stroke him a few times before taking him into your throat. Being hyper-aroused helps, you’ve little gag reflex at the moment, able to swallow him whole as his hips stutter upward.

His hands curl into your hair, rough grunts coming from above you.

“Good girl, just like that, nice and deep.” You suck and bob and stroke him until your jaw feels like it might come unhinged. He’s close, you can tell because he’s panting and tugging on your hair. “Remember what I said, don’t swallow.”

“Hmmm.” You hum in confirmation, vibrating around his dick and he jerks, cumming hard, pumping hot and thick into your mouth.

You do as your told, keeping your mouth on him until he’s done cumming. As soon as he’s finished, you pop off his length, wiping your chin with the back of your hand.

“Let me see.” Still breathless, he cups your jaw, prying your mouth open with his thumb. You can taste him on your tongue, feeling utterly humiliated as he inspects your mouth full of creamy white.

There’s a knock on his office door and you freeze, mouth open and skirt up around your hips. Sam looks you, patting your cheek. “Close your mouth, don’t swallow until I tell you. Now pull yourself together and sit up.”

You manage to get yourself into a presentable state, sitting next to Sam with your jaw clenched shut as he calls for Pepper.

“Come in.”

Your eyes go wide, looking at him in horror and he just grins right back, ticking his jaw as if you’re one of the sweetest things he’s ever seen.

“Good morning sir, I have your schedule ready and it’s a full day! Do you want to-” She stops cold when she sees you.

“Y/N,” she snorts. “I didn’t realize you were here this morning.”

You just shrug, lips glued shut, the taste of Sam filling your mouth.

“Well, doesn’t matter I suppose. Would you like me to order you a juice, sir?”

“Yes,” Sam nods thoughtfully. “Kale and turmeric, and whatever the spice is that they always add.”

“Of course.”

“Y/N,” Sam turns to you. “Would you like anything?”

You shake your head  _no_.

“I’ll go place the order. You have ten minutes before you need to be downstairs.” She looks at both of you and walks out of the room.

The second she’s no longer in view Sam leans over, close enough for you to feel his breath on your ear.

“Swallow.” He instructs. You comply instantly but it’s only a second before he’s asking for more. “Show me, tongue out.”

You turn to him, opening your jaw wide and sticking out your tongue, like a patient proving you took a pill.

“You really are made for this.”

-

The moment you’re up and walking your entire lower half is on fire. Your ass is still throbbing and the plug between your cheeks is a small but constant stretch.

The first meeting of the day is short, just a quick review of new building plans and the progress on the construction site where he took you yesterday. You sit next to him, barely able to concentrate on your useless note taking as your butt throbs against the rough fabric of the chair.  

Fifteen minutes later you’re trotting beside him heading to the next meeting. He stops just outside the conference room. Turning and picking an imaginary piece of lint off your shoulder. “Are you ready?”

“Yes.” You nod, clenching your ass, struggling to keep your eyes from fluttering shut. “What is this meeting?”

“The Jablonski case.” He explains, heading into the room. You follow him as the chatter of the conference room goes silent.

To your horror you’re met with Max, who offers you a sly little smile the moment he sees you. You want to die of embarrassment, sure that he will somehow be able to detect the dirty little game you and Sam are playing.

“Let’s get started.” Sam takes a seat at the head of the table and you sit next to him, nearly wincing in pain. He really did a number on you, but you can’t deny you love this, the feeling of your sore backside and the added bonus of the plug is a constant reminder of Sam and the effect he has on you. You rock to one side, subduing a gasp as you settle back in.

Max is the presenter and you’re grateful for the laptop, giving a reason to avoid looking at him for the bulk of the meeting.  

Sam doesn’t normally spend his time in a case review, it’s left to the more seniors members of the legal team, but this is a high profile case.  A billionaire client who’s been charged with a data protection breach.

You’re hyper focused, typing every word Max says. So focused in fact that when Sam leans in to speak, you flinch in surprise. He places the back of his hand over his mouth so that no one can see how close he really is, his lips nearly brushing the shell of your ear.

“How’s your ass?” He murmurs, sitting back and looking for your response.

You gulp, looking at the screen and type out:  _sore._

He nods as if you’ve just imparted some vital piece of information.

Leaning in one more time, he asks, “are you wet?”

You simply nod in confirmation.

He leaves you alone for the rest of the meeting. Nearly two hours of trying to sit still and play the part of some mysterious assistant. When it finally ends, Sam reviews a few of the details with Harry, a member of the senior legal team.

“Hey,” Max slides into the chair beside you.

You smile stiffly.

“I didn’t know you were working on this case. You should have told me.” He persists, eyes narrowing when you don’t respond. “Playing this one close to the vest, huh?” He leans closer, looking at Sam as he whispers. “Think you can get me some time with-”

“She’s not working on this case.” Sam turns in his chair, looking at Max who sits up straight, eyes widening. “Just a unique project that sometimes requires intense oversight. Tell me Max, how long have you worked for me?”

Sam engages in office small talk with a nervous but excited Max as you sit between them, tight lipped. The lucky thing about being with Sam is that people are much more interested in talking to him, than you. By the time they’re done you’re squirming in the seat, ass on fire, as Max pats the back of your chair.

“See you later, Y/N.” He gives you a little salute and leaves the room. Sam looks from the empty doorway to you, but doesn’t say anything.

-

By the time you are ready to leave the room, you’re sure Sam is going to be the death of you. You’re flushed with excitement, determined to do as he asked, to remain deserving of the reward. The door to the meeting room shuts behind you, and you hear the click of the lock.

“Hands on the table.” He instructs.

You bend over, spreading your palms wide, sliding forward.

“Does it hurt?” He asks, two big hands gently squeezing your cheeks through your skirt.

“Yes,” you hiss, turning your head to the side, pressing your cheek against the cool surface of the table. “It’s worse than last time.”

“Yes, it was.” You can almost hear the smile in his voice as he pulls your skirt up over your bum, exposing you to his hands once again. “But you like it?”

“I love it.” Your confession is more a yelp as he squeezes both cheeks in tandem sending immediate shocks of pain and pleasure right to your sex.

“How about this?” He carefully pulls your cheeks apart, tapping the head of the butt plug.

“It’s different…” You whine as he presses down with his thumb, forcing it just a little deeper. “I can feel it all the time.”

“Good.” He presses for a few more seconds and then you feel him wrap his finger around it, gently pulling back against your tight ring of muscle. You suck in a breath, wiggling despite giving your best effort to stay still. Then he’s pressing inward again, finally tugging harder than before and the plug slips out.

You groan, but remain silent as you hear him digging through his bag and then there’s the familiar click of a bottle opening. After a few seconds the re-lubricated tip of the plug is pushed quickly back inside you with a grunt.

“This will get us through to lunch.” He pats your ass softly. Just when you think he’s done, you feel his hand nudging between your thighs and his thumb is in search of your clit. Spreading your legs further, and inching backward you open up as wide as possible to give him better access as he begins to stroke your bud up and down at a slow, steady pace. “You’re always so wet when we’re together. Are you always like this?”

“I like the way you make me feel,” you manage, mouth gaping open as his thumb continues it’s tortuous journey over the most sensitive part of your body.

“The feeling is mutual.” He muses, dipping the very tip of his thumb inside your pussy, pressing downward to pull you open for him. It’s only a moment before he’s back to rubbing with even strokes.

“I’m getting close.” You warn him, pleasure coiling in your belly.

“Then we should stop. Don’t want to take away from the grand finale.” He pulls your skirt down, and turns you around with his hands on your hips, fixated on you with the eyes of a predator. “Open your mouth.”

You open up and he slides his thumb between your lips, closing them around his knuckle as you suck your own tart taste off of him. Looking up, you find him watching your mouth, his own lips slightly parted as you swirl your tongue around the pad of his thumb. When he pulls back, he wipes his thumb over your bottom lip, pulling down to see your teeth.

“We really are a good match.” He laments, swiping his wet thumb across your cheek bone. “Come on. I’m sure we’re already behind schedule and I don’t need Pepper pestering me the rest of the day.”

-

You make it to five-thirty. After the mid-afternoon break, where he more or less repeated the same inspection and few minutes of pleasure, you sat through a grueling business review watching the minute ticks by at a glacial pace.

As soon as the meeting is done he’s off like a rocket with you scrambling to keep up. You step onto the executive elevator, standing beside him as the doors slide closed. The moment the elevator begins its ascent he reaches over, swiping his key card and punching in a numerical code as the lift comes to an abrupt halt.

Before you have a chance to question what’s happening he’s pressing you against the wall, pinning you in place with the weight and heat of him.

One of his massive hands cups your breast through the material of your blouse, squeezing and groping with his breath at your temple.

“Oh,” you wheeze, a tender wanton whine escaping your lips as he touches you.

His hand leaves your breast just long enough to open your shirt, popping the buttons with such determination you’re afraid he might rip them off. That same big, warm hand slides inside your bra, pulling the cup down, then pinching your nipple between his thumb and forefinger.

Your teeth sink into your bottom lip as he presses harder drawing a long low whine out of your throat before taking your whole breast in his hand, massaging firmly. This is the first time he’s really  _touched_  you. Up until this moment, it’s been nothing more than calculated, well-placed touches but now you imagine what it would feel like to have his hands on your body, pulling you to him, exploring your skin. This is fast and urgent in stark contrast to the control you’re used to.

His free hand slides between your legs, lifting your skirt as he finds his way between your thighs.

“Are you ready for your reward?” He pulls back to look you. For the first time since this started, he looks as strung out as you do. He’s sweating as his tongue darts out to lick his lips.

“Please,” you implore, thrashing against the weight of him. You splay your legs wider, the material of your skirt riding up until it slides up your hips of its own volition.

Two thick fingers slide into your cunt, thrusting upward as he fills you for the first time. You’ve been worked up about this since the night in the hotel room, imagining what it would feel like to have him inside you, stretching you open.

“Fuck,” you gasp, banging your head back against the wall of the elevator with a resounding thud.

“Careful,” he warns, pulling his fingers almost all the way out of you, leaving just the tips inside. “Fuck yourself until you cum.”

You realize what he means. He’s not going to do this part for you, instead, you have to bend shaking knees, lowering your desperate pussy onto his fingers. Whimpering, you slide down the wall, his fingers filling you again before mustering the strength to stand back up.

“Come on,” he encourages, voice thick with desire. His hand gives your breast a squeeze, fingers curling into flesh “Don’t you want it?”

“I want it so bad,” you mutter, head rolling to the side.

Pooling every ounce of energy left in your system, you begin to slowly, painstakingly slide up and down, fucking your cunt on his hand like a desperate whore. After the first dozen wobbly attempts your lust begins to take over, giving you a superhuman strength to move faster, until you can hear the wet sound of your pussy taking his fingers.

He rewards your herculean effort by positioning his thumb just right so that with every pass it slides beside your clit, adding to the desperation. You’re still trapped between his hot, heavy body and the wall, drenched in sweat as you bounce  _up and down, up and down._

“Please,” rasping, you stop to make sure you don’t lose your footing. Both legs are quivering like jello, ready to give out at any moment. “I can’t get deep enough like this. Please, fuck me with your fingers.”

You’re sure he’s going to deny you, make you do it yourself. But much to your relief he waits for a beat and then thrusts his fingers so deep in your dripping cunt that he manages to get his knuckles past the lips of your slit. Buried deep inside he brings his thumb to your clit and rubs twice, all while pinching your nipple hard enough to make you cry out.

All it takes is two well place strokes and you cum around his fingers. Everything between your legs begins to throb, cunt tightening around his knuckles, ass clenching around the plug, pulling it deeper inside you. It’s intense and brutal, your body violently jerking as the waves of pleasure wash over you from head to toe.

The fingers inside you scissor open, staying wide as he pulls out, drawing every last sensation from your pulsing snatch.

He steps back just enough to let you wilt down the wall until your knees hit the carpet. You’re only half aware as he takes his cock out of his pants and shoves it into your mouth. Utterly strung out, you suck out of instinct, looking up to find him staring down, his mouth open in the blatant display of arousal he’s allowed himself.

Sam shoves forward a few times, tapping the back of your throat and cums, thick and salty over your tongue, sliding down your throat before you think any better of it. You don’t stop, licking the underside of the head, letting the flared crown slip gently between your lips over and over. Eventually, he holds your head in place, letting you suck for another minute before pulling himself free.

Fisting his cock he runs the wet head across your lips, tapping it against your mouth, taking a deep breath and then tucking himself back into his underwear.

You remain on your knees, trying to catch your breath. His hands on your face jolt you back to reality, thumb prying your mouth open.

“You swallowed.” He states calmly.

For a moment you don’t know what he’s talking about and then his list of expectations comes back to you.

“I’m sorry.” You murmur, looking up at him. “I don’t know if I’ve ever come that hard before. I couldn’t think.”

He snorts, chuckling as he reaches down, cupping your elbows to help you stand.

“I’ll give you one free pass.” He offers calmly, already composed. Your legs nearly give out and he grabs you around the waist, supporting most of your weight. “Are you going to be able to walk?”

“Yes, I just need a minute.” You breath, watching him watch you. It’s an uncomfortable feeling, having someone scrutinize you this up close and personal. It’s a unique brand of intimacy that Sam is well versed in.

When you’re able to compose yourself, he carefully goes about his routine of putting back together what he’s taken apart. He pulls your skirt down, buttons up your blouse and then carefully wipes at the maraca smudged under your eyes. His thumbs sweep across your cheeks wiping away sweat and tears, then he smoothes your hair back, tucking the few wild strands behind your ears.

“Thank you.” You hum lost in the feeling of his hands on your skin.

“You’re welcome.” He smiles thoughtfully, tilting his head to the side. “You keep the plug in until you get home. It’s up to you if you want to use it on your own time.”

“Okay.” You confirm.

“I’m leaving next Tuesday for San Francisco. You’re coming with me.” He instructs, stepping away from you, smoothing out his own shirt, then hair.

“I’m looking forward to it.” You nod. His tie is askew. Before you stop to think you reach out, adjust the knot until it’s back in place. Realizing your actions you wait to see if he’ll correct you, but instead, he just watches silently as you slink back beside him.

“Thank you.” He remarks touching the tie with two fingers.

“You’re welcome.”

-

_Parts **Seven and Eight**_ are currently available on [Patreon](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) for a monthly pledge of $2.50. This includes early access to all my stories and Patreon exclusive content.  >> [CLICK HERE](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) << 


	7. Seven

“You made it!” Max claps his hands together.

“Yeah,” you smile walking toward the table. Half the bar is filled with the staff from W & S.  

He’s clearing off a chair for you next to him, directly across from Pepper who looks like she’s already had a few.

“What is she doing here?” Pepper groans.

“Play nice, Pep. We’re all friends.” Max gives you a shit-eating grin, pulling the chair for you.

“The last thing I need is her running to the boss, tattling about how his assistant complains about him.” She looks from you to Max.

“I’m not a snitch.” You settle in as Max pours half his beer into an empty water glass and slides it front of you.

“We’ll see.” Pepper purses her lips, giving you a once over. “Sam has a way of turning people on each other. Everyone needs to survive in the end.”

“He can’t be that bad.” Max rolls his eyes.

“Ask Y/N,” Pepper scoffs, sitting back in her chair. “She’s in tears every time she leaves his office.”

You want to melt into the floor.

“I, um, he’s just-” you sputter, searching for the right words. “Sometimes he gets a little…intense.”

“That’s one word for it.” Pepper snorts, martini sloshing over the edges of the glass. “You know,” she points at you, “I have a theory about what he’s got you doing.”

“Oh yeah?” You’re just about done with tonight and you only just arrived. You thought this might be fun but instead it’s an exercise in hiding your reactions. Not to mention Max failed to mention your sworn nemesis would be here.

“Internal employee audit.” She nods. “He’s got you keeping track of something across departments. If I had to guess I’d say he’s looking for something. Maybe…a mole? A leak?”

“Are you spying on us?” Max laughs, placing a hand on your back.

“I’m not supposed to talk about it.” You look around for a waitress, you’re going to need a stronger drink.

“Give us something.” Max shakes the back of your chair.

“I don’t do many things well, but I can keep a secret with the best of them.”

“Hey Pepper,” Doug chimes in from the other side of Max. “Does Winchester ever talked about his brother?”

“His brother?” Your interest is peaked.

“You don’t know about Dean?” Pepper cocks her head. “Sam’s brother is on the FBI’s ten most wanted list.”

“For what?” You’re flabbergasted, you guessed there were some dark secrets in Sam’s past but you didn’t expect a fugitive to be one of them.

“Murder, kidnapping, robbery, you name it.” Pepper shrugs, fishing an olive out of the bottom of her glass. “Every once in a while an agent shows up at the office to ask him questions.”

“Here.” Max pulls out his phone, pulling up the information. “Dean Winchester, unlawful flight to avoid prosecution. Wanted on five counts of murder, one count of kidnapping…where’s the good stuff - here we go -  grave desecration, impersonating a federal officer, torture…the list goes on. The guy is a real piece of work.”

“Wow.” You take the phone from Max to look at a photo of a handsome guy in an orange jumpsuit. “That’s crazy. Sam’s been so successful and his brother is…this.”

“I guess their dad was some crazy, backwoods survivalist type. His mom died when he was a baby.” Pepper nods. “The story goes that Sam got as far away from his dad as he could. Got himself into Stanford. His senior year Dean showed up and killed Sam’s girlfriend. Burned the whole apartment building down with her inside.”

“Are you serious?” You’re horrified, looking from Pepper to Max. “His brother killed his girlfriend? Why?”

“I guess Dean wanted Sam to ditch school and go with him and their dad.  When Sam refused, Dean went off the deep end.”

“Holy shit,” you breathe, handing Max’s phone back to him.

“That’s why he’s so uptight about everything. The man is brilliant but he’s fucked in the head.” Pepper raises her hand to find a server. “I need another drink.”

–

“Really, I’m fine.” You stop in front of your apartment building. Max insisted on walking you home for safety but you get the distinct impression he expects to be invited up.

“There could be creeps out here.” He shrugs, looking at the steps of your building. “You tired? Up for a nightcap?”

“I don’t think so.” You shake your head. “It’s late and we’ve both been drinking.”

“What’s the worst that could happen?” He grins, all charm and white teeth. He’s handsome and cocky, and in another lifetime you’d take him upstairs and ride him until he popped like a champagne bottle.

“No hypotheticals.” You step back and he moves forward in tandem.

“Come on,” he grins, leaning closer. “We both know we’d have a lot of fun together.”

He goes to kiss you, but you stop him with two hands on his chest. “I told you I was seeing someone. And you told me we were out tonight as just friends.”

“Seriously?” He cocks an eyebrow. “I thought you were just trying to play hard to get. Why are you out with us on a Saturday night if you’ve got a guy?”

“None of your business.” You pat him on the shoulder. “I’m going upstairs and we’re both going to forget this ever happened.”

 

**TUESDAY**

“Good morning.” Sam greets you without looking up from his tablet.

“Yes, good morning.” Pepper sneers, looking up from her laptop long enough to give you the stink eye. “Boarding begins in five minutes. You’re cutting it close.”

“I got stopped by TSA,” you explain and Sam smiles without looking up. “Random check, I had to have the hand swab and they searched my bags.”

“Early is on time.” Sam looks up at you, giving you a once over.

“And on time is late.” You parrot back. “I’m sorry Mr. Winchester, it won’t happen again.”

“Better not.” He confirms.

W & S owns two planes, both of which are in use. Sam’s not one to shake up a finely tuned system. While he could simply bump the legal team, he won’t. Schedules were solidified and this is a last minute trip, so today he’s flying Delta with all the other lowly non-millionaires.  

The first class section is separated into pods. There are a few singles and the rest are in pairs, with ample leg room and enough space to fully recline the seat if one wants to sleep.

You’re struggling to get your ticket out of your purse to check your seat number when Sam grabs your arm, thumb and forefinger pinching just above the elbow. “You’re here. The window seat.”

“Um,” You look around as if he’s the one who’s confused. “I’m in first class?”

“Don’t be ridiculous.” He rolls his eyes, already impatient. “Sit down.”

You take your seat, sinking into a pod large enough to hold two of you.  _This is how the other half lives._

“I’m up here…with you.” You state the obvious, watching as the few other people in the section find their seats.

“Yes, you are. God, I hate flying commercial.” He shudders, retrieving his computer from his briefcase. “Would you have preferred to sit in back with Pepper?”

“No, but…doesn’t it look strange that I’m up here?”

“Things look however you want them to look,” he snips, putting up a finger to call over a flight attendant. “Next time I’ll make sure you’re back in the cargo hold if that would make you more comfortable.”

“What can I get you, Mr. Winchester?” the stewardess asks, smiling sweetly.

“Two blankets, two waters,” Sam orders, turning to you as she walks away. “Stop fidgeting.”

“Sorry.” Sitting back you force your legs to stop bouncing. “I’m not the best flyer. I get nervous.”

“Lucky for you I have a few tasks to take your mind off things.” A small smile appears for a fleeting moment. “Just try to relax.”

The plane boards and the minutes tick by. While you’ve flown plenty of times it never gets any easier. And today is worse. Sam makes your senses heightened. Normally it’s just sex, but today it’s also fear that’s swimming in your belly, churning like a swell rolling toward shore.

The attendant brings Sam two thin blankets which he passes off to you.

“Thanks.” you whisper, unsure. “You think I’m going to be cold?”

“I think,” he leans in your direction, close enough that no one else will be able to hear, “that you’re going to have that skirt up around your hips and your hands between your legs for most of the flight. So unless you want the flight crew to see your pussy, you’ll want the blankets to cover up.”

“Oh.” You look towards the crew who have been stealing glances at Sam since you boarded. “But…they’re watching us.”

“This is a perfect opportunity for you to learn the true meaning of discretion.” He buckles his seat belt, wordlessly reaching over and doing the same for you. He grabs one side, then the other, sliding the clip into the buckle, tightening it around your stomach as if you were a toddler. “Now cover yourself and pull up your skirt. We’re about to take off.”

He logs onto his computer, checking his email one final time.

Carefully unfolding both blankets, you lay them over your lap, before subtly hiking your skirt up until your bare ass is directly on the seat, then fold your hands together in your lap as the plane picks up speed on the runway.

“Fuck,” you whisper, closing your eyes at the sensation of the front wheel leaving the ground.

“I think  _nervous flyer_  is an understatement.” Sam observes.

“I’m not normally this much of a baby. I was on a bad flight once,” you whisper eyes closed tight. “I was a teenager and I was flying alone. The turbulence was so bad people were crying, we all thought we were going to die.”

“Well, you’re not going to die today.” One of his big hands curls over both of yours where they’re clutched tightly in your lap.  You’re so startled by the compassionate touch that you flinch and he squeezes harder.

Slowly, the plane gains altitude and he releases your hands. Looking around carefully to make sure no one is paying attention he leans over, voice low as he murmurs into your ear.

“I want you to rub your clit for the next five minutes. Nice and slow, nothing too fast. Tell me when you’re wet.” And with that instruction, he sits back in his seat. A thrill shoots up your spine at the challenge of complying with the request.

You look around, checking to make sure no one is paying attention and snake your hand under the blankets, sliding over your pussy. It doesn’t take much movement to do as he asks, just the pad of your finger moving back and forth over your clit, slow and even. Sam pulls out his phone, starting a timer for five minutes and you think you might die of embarrassment.

It’s truly an exercise in restraint. Your jaw is locked in place, trying your best to maintain a neutral expression as your own touch begins to stir excitement between your legs. A familiar tingle blossoms from your cunt up to your belly.

It doesn’t take long, there are still two minutes on the timer when you swallow hard and lean toward Sam and whisper, “I’m wet.”

“Already?” He tilts his head to the side to look at you, pulling his glasses off. He smirks, eyes dropping down to where your hand is moving imperceptibly under the blanket. “Two more minutes, keep going.”

Instead of watching the seconds tick by you close your eyes and concentrate on keeping your face from giving away your dirty little secret. You think about Sam, how badly you want his hands on you and what new experiences will happen over the next three days. You’re here for two nights and you wonder if he’ll want you to spend all your time with him, or if he’ll send you away as soon as he’s had his fill, like the first night you touched yourself for him on his hotel bed.

“Times up.” He announces. And you take a breath, yanking your hand away. You’re pretty good at knowing how to touch yourself. He’s given you ample practice, all those mornings and nights of denial, getting yourself right to the edge are paying off. You just hope he’s not expecting you to cum, not here.

“Can I have some water, please?” You clear your throat, gesturing at the two bottles tucked into the pocket in front of him.

“Of course.” He opens the bottle, holding the cap and hands it to you. “You have ten minutes, then we go again.”

You sit stoically next to Sam as he reviews documents, unphased by the fact that you’re right there, next to him, shifting in your seat. Time ticks by and he leans over again, looking away from the screen as an afterthought.

“Five minutes, touch yourself the entire time, don’t cum.”

“I will.” You look at him, his stare sending little zaps of anticipation to every inch of you.

This time he watches you, glancing up every so often to ensure privacy. From your seat no one other than Sam can see below your neck but controlling your facial expressions is proving the hardest part of all. As your finger brushes over your clit again and again. You lock your jaw, it’s the only way to keep your mouth from falling open. At one point your eyes flutter shut, but he doesn’t like that.

“Look at me.” He commands, voice low and confident as you turn your head to look him in the eye. “We’re just two people having a conversation. No one knows otherwise.” He glances down to where your hand is moving gently under the blanket. “When’s the last time you came?”

“When I was last with you,” you confirm in a breathless whisper, pleasure steadily building.

“Did you touch yourself after that?”

“Yes, twice.”

“But you didn’t cum?” He smiles, shifting in his seat to give you his full attention. “I don’t remember giving you any homework.”

“It was so good last time.” You take a deliberate breath, pausing to control your throbbing pussy before you continue. “Making myself wait for you made it so intense when I finally came.”

“I’m glad to hear it was so good for you.” His mouth barely moves as he speaks, pressing his hand over the crotch of his pants to adjust himself. “From now on you don’t cum unless I give you explicit permission. You’re to ask every time. That wet little pussy is mine and so are your orgasms. Am I clear?”

“Yes,” you hiss, fingers slowing. Rubbing yourself is hard enough, but listening to him talk like this is almost enough to make you cum all on it’s own. “I need to stop.”

“You still have a minute left. You better not stop.” He chastises, frowning as if you’re a petulant child in time out. “Just slow down and control yourself. Deep breaths.”

“I’m gonna cum,” you rasp, staring at him as a tear slides down your cheek. Your hand is shaking, middle finger pressing against your aching bud. “Please, I can’t-”

“Don’t you dare.” Sam looks at his watch. “Just a little bit longer. You won’t like what happens if you disobey me right now.”

“I’m trying so hard, but I can’t-”

“Times up.” He taps your knee and you instantly pull your hand out from the under the blanket. You’re one firm touch away from falling over the edge, your pussy is slick, dripping with arousal and you can feel it on the seat under you.

“Everything alright over here?” There’s suddenly an attendant standing next to Sam, looking at you with concern.

“Nervous flyer.” Sam explains, patting the back of your hand. “Panic attacks.”

“I’m fine,” you offer, voice shaking as you wipe sweat away from your forehead. “It’s just nerves.”

“Please let me know if you need anything.” She nods, giving you one last look before walking away.

“You’re attracting attention.” Sam chuckles, as your cheeks burn bright red.

“I was trying to be discreet,” you puff, sitting back in the seat.

“Trying and failing.” He points out the obvious. “But by the time I’m done with you, you’ll be surprised what you’re capable of suppressing.”

There’s no response for that. It’s terrifying to hear that for him this is just the tip of the iceberg. But it’s also exciting, everything about this arrangement is exciting. The fact that he has you edging yourself on a plane, surrounded by people and manages to remain so casual about the whole thing makes you want him even more.

There are three more sessions. Each farther apart than the last as he gives you ample time to calm down. By the time you’re finished with the last session the world is blurry, your entire body sweating and quaking as you use every last ounce of self-control to hold back an orgasm.

It’s just as the pilot announces that you’ve been cleared for landing that Sam closes his computer and starts to roll up his sleeve as if he’s about to go to work. The flight attendants strap themselves into their own seat and Sam tilts his head toward you.

“Spread your legs.” He murmurs, turning to watch your face as you comply. He snakes the hand closest to you under the blankets, wedging his knuckles between sticky thighs. His eyebrows shoot up when he feels how wet you are.

The plane begins to shake as you hit a turbulent patch and at the same time his finger slides over your swollen clit. You almost shout out, instead slamming your eyes shut and gripping the armrests.

“You love this don’t you? Being on display for me, everyone else just going about their lives ignorant to what’s going on between your legs.” The heel of his hand presses over your clit as he scoops down, sliding two fingers into your throbbing cunt. You whimper, sinking teeth into your bottom lip.

His fingers slide out and up, stroking your clit before burying back inside. He does it again and again, finding a rhythm, stroking your bud and teasing your hole open until you’re a mess, squirming uncontrollably.

“You’re gonna make me cum.” You wheeze, trying to squeeze your legs together.

“You better not.” He warns, hand slowing to make slow, painful circles around your clit.

“I’m trying but it’s too much.”

“Then we better stop.” He quips, pulling his hand away, leaving you gulping for air as the plane’s wheels touch down on the tarmac. “You did well.”

“Thank you,” you whisper, smoothing your hair back, ignoring the constant throb between your legs.

You put yourself back together, unlocking your seatbelt and pulling your skirt back into place. Right on cue, Sam hands you a napkin that you use to wipe off the seat under you, blushing as he watches you clean up the mess you’ve made.

In stark contrast to your usual roles, Sam stands up grabbing his own carry on bag, then takes yours, throwing the strap over his shoulder.

“You good?” He looks down, offering a hand to pull you up.

“Yes, thank you.” You nod, following him down the aisle.

The stewardess offers you a little pout, gently touching your shoulder as you pass by and a moment later you step off the plane into the San Francisco airport.

-

_Parts **Eight and Nine**_ are currently available on [Patreon](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) for a monthly pledge of $2.50. This includes early access to all my stories and Patreon exclusive content.  >> [CLICK HERE](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) << 


	8. Eight

Your hotel room is a long elevator ride up at the Four Seasons. It’s twice the size of your apartment and the mattress is the most comfortable thing you’ve ever felt in your life. 

Sam’s big meeting isn’t until the morning, but he had plenty to go over with Pepper so you were sent to your room until he calls for you. You take a shower and order room service for a snack, then sit at the end of the bed and watch TV as the hours tick by. 

By the time he texts you, you’re beyond ready and full of nervous anticipation. Every inch of your body is lotioned and soft, hair curled and makeup minimal but enough to add a little oomph to your everyday look. 

Picking up the phone you read the message from Keith Campbell. 

_**Open your gift and put it on. Come up my room. Wear a dress, we’re going out.** _

“My gift?” you mutter. There’s a knock at the door right on cue. You collect a box from the bellhop, thanking him and kicking the door shut behind you. The box itself is wrapped in nondescript, white paper and you tear it open to reveal a pearly iridescent box with the name _Dark Garden Lingerie_ scrawled across the top. 

Inside is a matching black bra and panties. Upon closer inspection, you discover the panties are crotchless, and a thrill of anticipation runs up your spine. There are garters and thigh-high pantyhose underneath them and you take out the full set, stripping down to try it on. 

It takes a few tries to get it right, but when you’re done you admire yourself in the mirror. The garter sits smoothly around your waist, the rest of the set perfectly in place. It dawns on you that Sam knows your measurements. He paid close enough attention to be able to order lingerie that fits like a glove. He’s given this thought, took the time to pick out something specific to his tastes. This little delivery was pre-planned. 

For the first time, you wonder if he thinks about you with the same fascination you have for him. Not wanting to indulge those thoughts you focus on the matter at hand. 

You’re better prepared this time. You overpacked, and have something you think will be perfect for the occasion. It’s a bright red one shoulder cocktail dress that falls just above the knee. It’s daring but also conservative, a commentary on Sam if ever there was one. 

-

Waiting in the hallway you knock on Sam’s door, shifting from one foot to the other. The uncertainty of your time with him makes your blood run hot, a tingle that always sets in when you know you’re about to see him. 

The door swings open and there he is in an expertly tailored navy blue suit that was clearly made for him. It’s easy to get caught up in who he is and your relationship with him, but all that aside, he’s a devastatingly handsome man. 

He stands there with his hand on the door, inspecting you from head to toe before stepping aside. “Come in.” 

You step into his room and he shuts the door behind you. 

“You look beautiful,” he comments, stalking around you in a full circle. 

“Thank you for my gift.” You lick your lips as he comes to stand in front of you. 

“You’re wearing it?” He grins. 

As if he even needs to ask. 

“Yes,” you confirm. “Would you like me to show you?”

“Not right now. We’ll save that for later.” He steps closer, lifting his hands to curl around the back of your neck, his thumb resting in the dip between your collar bones. All of his fingers stroke up the back of your neck, sending a spine tingling chill from head to toe. He rarely touches you, so the feeling of his warm hands lingering on your skin is a treat. 

You look up as  he stares down at you and the world narrows down to this moment. His fingers press on the base of your skull, thumbs pressing softly at your jugular notch as you stare at each other. 

This is by far the most intimate moment you’ve experienced with Sam. He’s close and quiet, inches from your face, close enough that you can feel his breath. It’s as if you’ve been drugged, willing to do anything he asks of you. One of his thumbs moves up to press at the front of your throat, feeling you swallow. 

“I’m going to take you to dinner,” he whispers, mouth getting closer by the second. His lips brush the corner of your mouth as he speaks. “And then I’m going to bring you back here and fuck your tits. Would you like that?” 

“Yes,” you whimper, eyes closed as you swim in the feeling of him. 

“I’m going to test your limits tonight, Y/N.” Your legs feel weak as he speaks, knees threatening to give out. “Some things may hurt but I promise you’ll like it all. Do you trust me?”

“Yes,” you whisper, mouth falling slack. 

“If you’re good for me tonight, tomorrow I’ll fuck your pussy,” he murmurs, his mouth moving to the shell of your ear. “I bet you're so tight. Bet that wet little cunt is just begging for a cock.” 

You wheeze, breath rattling in your throat as your sex begins to tingle. Part of you thought maybe he’d never actually fuck you. That this is all some power game designed to make you crave him but never actually give you what you want. If it means he’ll fuck you, you’d crawl on the floor and bark like a dog if he asked you to. 

“I’ll be good.” This pledge comes out as a whine, strained and low as he pulls back to look at you. 

“I know you will,” he affirms. “Now let's go have something to eat, shall we?” 

-

You slide into the backseat of a sleek, black car and Sam settles in next you, immediately rolling up the privacy window that separates the back from the driver. You’ve barely pulled away from the curb when he reaches over and hooks a hand under your knee, laying your leg over his thigh, effectively opening you up for him. 

You don’t say anything just turn to watch him as he’s focused on his where his fingers are trailing up your inner thigh, brushing gently up past the thigh highs and garter clips, until he finds exposed flesh. You suck in a breath and he grins like a wolf, refocused on whatever new torture he has in store. 

“Are you wet?” he asks softly, fingers moving closer to your trembling apex. 

“Ahuh.” The second the word leaves your mouth you tense up, and you feel a slap on the inside of your thigh, just above the knee. 

“What did I say about talking like that?” he chastises, looking for your confirmation. 

“I’m sorry. I meant _yes_. I’m wet.” Squirming in the seat you draw in a breath and try to sit still. It seems an impossible task with his hand inching up further and further and then you feel it. The tips of two fingers easily find the obscene hole in the crotch of your panties, sinking into your wet flesh up to his first knuckle. 

“Yes you are,” he shakes his head. “What about today turned you on the most?” 

“The plane was challenging,” you gulp. “But when you tell me what you’re going to do to me later, I love that. And I like when you touch me.” 

“Of course you do,” he coos, his thumb finding your clit, rubbing over it lightly. 

You jerk as he grazes the most sensitive part of you. You’ve been throbbing since the flight and this might prove to be your undoing. 

“I’m gonna cum if you keep doing that.” Your mouth falls open, fighting the urge to close your legs around his hand. 

“That’s not the way to ask.” He presses harder at your clit and you groan as his fingers sink deeper inside you. “What you meant was _may I cum?_ ”

“May I cum?” you rasp, shifting in the seat, canting your hips forward for relief but it only makes it worse.

“Absolutely not,” he quips, giving your clit one last press before removing his hand from between your legs. “Open your mouth.” You do as he says, jaw falling open as he slides his two sullied fingers over your tongue. “Suck.”

You can taste your own pussy on him. This act elicits a kind of strange arousal that you never knew would turn you on until he did it the first time. As he begins to slide his fingers deeper, you wonder if he’ll ever have you suck his cock after he fucks you, make you swallow his shaft, coated in your slick. 

His fingers push deeper and you gag for a moment before regaining control, opening your throat so that he can push as deep as he wants. You’ve taken his cock deeper than this, but it’s an altogether different feeling to have his fingers wiggling in the back of your throat. 

“Look at me.” He commands and you snap to attention, wide-eyed while he fucks your mouth with his fingers. A tear slides down your cheek, as you clench your thighs together. Your throat makes its own unique squelching sound and it’s enough to make your cunt clench, the thought of him using you like this is filthy and beyond exciting. 

“That’s enough for now I think.” He removes his finger from your mouth and you close your eyes, trying to pull yourself together. He plucks a kleenex from his pocket and wipes his hand off before lifting your leg off him. 

\--

“You know,” he leans back in his seat, sipping a glass of seltzer. “It used to be when I went on these trips I’d eat alone or order room service. Having you here is far more entertaining.”

“I’m glad you’re enjoying our arrangement.” You smile, crossing your ankles under the table. “Can I ask you something?”

“You can ask,” he volleys back. “But I may not answer.”

“Why don’t you drink alcohol? Is it just the whole health thing?”

“Partly,” he concedes, setting his drink on the table but keeping his hand over it. “Alcohol does a lot of damage to your liver over time. But more than that, I am in complete control of myself. Aware of my surroundings. There are dark things in this world, bad things happen all the time and most people never see it coming. After something terrible happens people tell themselves there’s nothing they could have done, but most of the time that’s just a load of shit. There’s almost always more that can be done. They could have paid attention, been more careful, worked harder. I don’t drink because I want to see what’s coming.” 

“Well.” You sit back. “I thought you were just gonna feed me some line about being on Keto or something.” 

He laughs at that, a deep laugh that puts a genuine smile on his face. 

It makes sense from what you know about him professionally and personally. At W & S there are people coming at him from all sides, there’s always a new offer, a pitch for the next great idea. And after what Max and Pepper told you about his girlfriend and brother, this falls right in line. The rug has been pulled out from under him before, he’s not about to let it happen again. 

“I have a question for _you_.” He sits forward with that trademark soul-piercing stare. 

“Okay.” You nod. “I’m an open book.”

“What were you doing delivering mail?” He looks genuinely perplexed, eyes narrowing. “I know you said that you wanted experience in a professional environment, but why not a receptionist? You’re intelligent, attractive, well-spoken when you want to be. What brought you to the W & S mail room?”

You’re quiet for a moment, looking down at your hands folded in your lap. You look back at him before you speak. “You did.”

“What do you mean?” His interest is peaked. 

“I worked in a factory, by choice more than anything. I can work hard when I need to, but the truth is I hate it. I’m a daydreamer by nature. Anyway, I was watching my life pass me by. One night I was scrolling on Facebook and came across your TED Talk, the one you did in Palo Alto. You talked about personal accountability and making changes and committing to them. It was what I needed to hear at that moment. I Googled you, found out your firm was in Boston and I applied for the first job I thought I could get. Not because I was trying to get close to you, or anything stalkery, just because I wanted to be around that kind of energy. I spent the last twenty-eight years around stoners and dropouts. I’m ready for more.” 

“Really?” He grins, looking at you with some kind of new found appreciation. “So there is a little bit of a go-getter in you.”

“You have no idea, Mr. Winchester,” you tease, leaning toward him. “With the proper motivation, I bet I could do just about anything I put my mind to.”

“I’ll take that as a challenge.” He lifts his chin in your direction. 


	9. Nine

“ _Uhhhh_ ,” you whine, tugging on your arms where they’re tied above your head, secured to the headboard. You can’t form full words with his tie stuffed in your mouth, not that you would be able to talk anyway. The only thing you can focus on is the delicious throb of your nipples, each one crushed in a vice grip between his thumb and forefinger.

The world is black, blocked out by a velvet blindfold that’s over your eyes. While you can’t see him, you can sure as hell feel him, the weight of him as he straddles your ribs, knees tucked into either side of your body.

His cock is thick and heavy, laying between your breasts as he tugs on your nipples, pulling then twisting, sending little jolts of pain from your tits right down to your soaked pussy.

Sam is slowly and surely opening up a whole new world for you. If anyone else had said that you’d enjoy pain, and loss of control during sex, you’d have scoffed at them. But right now you’re more worked up than you’ve ever been in your entire life. You’re completely at his mercy, trussed up and laid out, about to defile you in yet another salacious act that makes your blood run hot with anticipation.

“Are you going to be good for me?” he asks, twisting your nipples viciously as you arch up with a muffled shout.

“ _Ahmm_ ,” you nod eagerly, rubbing your thighs together, feeling the evidence of your arousal all over yourself.

“Do you trust me?” he asks, letting go of one nipple to bring the free hand up to hold your jaw still.

“ _Hesh_ ,” is all you can manage, somewhat nervous at the fact that he’s asked you this question twice in one night.

“I know you like it when I spank you.” He abandons your jaw in favor of pinching both nipples in tandem. “And I can tell you like this because your cunt is drooling like a bitch in heat.” He tugs upward and your neck snaps back, pain spiraling downward and turning into pleasure somewhere along the way. “So we’re going to try something else tonight.”

Both hands leave your breasts and the weight on top of you shifts as he leans toward the nightstand. While you don’t know the exact inventory, you listened to him set various things on the table next to the bed as you laid bound and blindfolded waiting to begin.

He moves back into position, the silky soft head of his cock resting on your chest. He pinches your left nipple, squeezing hard several times until it’s impossible to make the sore peak any harder.

“Deep breath in.” He instructs. You suck in a breath through your nose. Cold rigid metal sinks into either side of your nipple, tiny little teeth biting into the tender flesh makes you scream into the gag, your entire body undulating underneath him.

“Ssshhh,” He quiets you, cupping the base of your breast. “One more to go.”

While it hurts unlike anything you’ve experienced before, it’s an erotic pain that leaves you wanting more. You can’t exactly explain the neediness blossoming between your legs as he begins to tweak the opposite nipple.  This time you know what’s coming, and prepare yourself as the little teeth bite into aching flesh.

Both nipples clamped, Sam admires his handiwork, pushing both full tits together, trapping the head of his dick between them. There’s a constant throb in your nipples, just the same as your clit, pulsing between your legs and it’s sparked every time he jostles your breasts.

“You’re breathtaking like this.” Sam’s voice is soft, full of genuine admiration as he squeezes the base of each breast. “There are screws on the side of the clamps. If I turn them, the clamps will tighten.” He explains calmly. “Do you think you can take a little more for me?”

His question, while degrading and frightening, is exhilarating more than anything. The idea that you’re doing this for Sam, trying to be good and accept some sort of “punishment” that in reality, you’re craving, makes you quiver with excitement.

“ _Hesh_ ,” you agree, shaking in anticipation.

He slowly moves to one clamp, you feel it the second he turns the screw. It tightens down and a sharp pain bursts to life. It’s almost too much but he stops just short of tipping over the edge and you pant through your nose, tears sliding from both eyes, down your temples.

“Too much?” he inquires.

“ _Ooo_.” You shake your head  _no_.

“I knew it.” There’s a smile in his voice as he carefully tightens the other clamp until you’re bucking between his legs. All you can focus on is the pain in both breasts, this wonderful new torment you never knew you wanted. You’ve all but forgotten there’s a naked man, twice your size, straddling you.

He reaches for the table again and there’s the click of a bottle and the sensation of a self-warming lube being drizzled over your breasts. The bed shifts as you hear him stroke his cock a few times.

He slides his cock up between your breasts while pushing them together. The clamps move gently but it’s enough to draw a whine from your throat, the pain and pleasure mixing together as he begins to fuck your tits with long, drawn-out thrusts.

“I bet I could make you cum from playing with your nipples.” He muses, sliding his thick cock easily up until the head taps under your chin. “I’ll try that some other time. Tonight is about what I want from you. And you’ve yet to disappoint me, Y/N. You always obey so well.”

You want to respond, tell him how badly you want to be good for him, explain this need to do as he asks, to follow orders and please him, but all you can do is moan into the gag.

The throbbing in your nipples lessens over time as the clamps slowly cut off the blood flow and by the end, there’s very little pain, only a dull pleasure that keeps your pussy wet and eager to make him happy.

He’s squeezing your breasts together hard, huffing above you as he titty fucks you like he’s part of an Olympic event, his balls rocking into the underside of your boobs with each pass.

Without warning, he pulls the tie out of your mouth.

“Open up.” He instructs and you comply. Two more thrusts and he shoots warm and sticky over your chest, chin, nose, and open mouth, spurting again and again until you’re covered in pearly white. “Fuck,” he grunts, stilling his movements before releasing your breasts.

You lay there, arms tied, mouth open until you feel him scooping cum off your chest and his fingers sliding into your mouth for you to suck his seed off them. When he’s had his fill of watching you swallow, he removes the blindfold and there he is above you.

His hair is wild, hanging around his face, cheeks bright pink from arousal and exhaustion. He grins, watching as you blink at the bright light of the room.

“We’re not done yet,” he teases, his eyes dropping down your breasts and you follow. Your nipples are dark and suddenly painful as you see them, still in the grips of each clamp. He releases one and the blood flows back into your peak, bring with it a new pain that makes you howl in response. Before you can catch your breath he unclamps the other one and you’re thrown right back into the throes of it, wiggling under him, desperate for some relief.

“Do they hurt?” he asks, eyeing your abused tits, licking his lips.

“Yes,” you confirm. “But I like it.”

“I’m glad. You look perfect tonight….beautiful.” He swoops down, closing his lips around one of your aching nipples. You watch the truly erotic sight as his mouth closes around the bud and the wonderful warm sucking sensation as he latches on. After a moment your eyes flutter shut, reveling in the feeling of his mouth on your body for the first time. When he pulls away you fear it’s over but then he’s sucking on the other one, rolling the peak between his teeth and sucking until you’re about to come undone.

He was right, he probably could make you cum like this.

As always, he knows when you’re close. You moan in protest, eyes popping open as his mouth leaves you.

“Let’s see how the rest of you is doing.” He smirks, re-adjusting himself so that he’s kneeling between your spread thighs. While you can’t see your pussy, you can feel what a mess you are. Your cunt has been throbbing on and off all day and this last hour has pushed you beyond aroused.

“I’ve never seen anyone this wet before,” he comments, gripping both thighs, thumbs digging to keep you open. His observations never fail to make you feel somewhat humiliated, embarrassed at how desperate you are for more of what he has to give.

“Your poor little clit looks swollen,” he muses and you half want to crawl under the covers.

Then you feel his thumb on you, looking down to watch him touch between your legs. The first brush with the pad of his thumb sends your body bucking upward, simultaneously trying to get away and pleading for more.

“Oh fuck,” you rasp, tugging violently at the restraints as he begins to rub your clit, slow and gentle. “Please, can I cum? Please?”

“No,” he says with conviction. “Not tonight.”

“Please!” You cry out, the pleasure is building, stoking a spark that’s been on edge all day.

“Stop and breathe, control your body,” he instructs. His thumb is still pressing over your bundle of nerves. “You know the rules, no orgasm until my fingers or cock are in this sweet cunt.”

“I can’t,” you plead, feeling the tears coming again, body jerking from side to side.

“I said  _no_.” His voice booms, still trying to push you over the edge.

“You’re gonna make me cum like this, please, oh please…”

At some point, your own voice becomes a blur, the sound fuzzy in your ears. This is a new level of desperation. You want so badly to be good for him, to obey his rules but trying to hold back seems futile. You can’t stop yourself and the tug of war is too much.

It barely registers when he stops touching you. You’re crying, tears streaming as you sob with need, left right on the edge.

There’s a rush of feeling back in your arms as he unties you, and slides up to lie beside you, one hand spreading wide over your belly and pressing down.

“Calm down.” His voice is at your ear, low and even. “Stop crying, take a breath.”

You do as he says, eyes shut tight as you suck in a couple of deep breaths, easing back down from the ledge.

He’s hot beside you. Warm naked skin pressed into your side, his hand on your stomach keeping you grounded.

“I don’t know what that was,” you whisper, wiping your cheeks. You open your eyes to find him looking down at you inquisitively. “I’ve never burst into tears during sex before.”

Sam chuckles, raising his eyebrows. “I have a way with people.”

“I wanted to be good for you and I thought I wasn’t going to be able to stop myself,” you confess, feeling utterly small and uncomfortably vulnerable laying here in his bed.

“You were good for me,” he affirms, his eyes dropping down your body to take stock. “I told you I was going to test your limits. We found one.”

You quiet, feeling his hand on your belly rise and fall with each breath.

“The rest was…” You widen your eyes, almost laughing from the nervous energy of the comedown. “Intense. But I liked it.”

“Good.” His eyes narrow, the hand from your stomach reaching up to your face to push your sweaty hair back from your temple. The gentleness of the touch is at odds with his usual coldness. He looks at you for a moment, something fleeting coming then going just as quick as it was there. “It’s time for you to go back to your room.”

Your stomach sinks, every bit of arousal that’s culminated throughout the day drains away with those words.

“Oh,” you nod, getting onto your elbows. “Okay.”

You sit up, swinging your legs over the edge of the bed. There’s no way you can hide your disappointment but at least you can get out before he calls you out on it. You pick up the discarded bedspread off the floor looking for your dress, unable to find it until you turn around and Sam is standing, stark naked, with it in his hands. You try to take it from him, but he stops you, grabbing your bicep.

“I would let you stay.” His eyes search yours, remaining unreadable as always. “But Pepper will be here in a few hours.”

“I understand.” You nod but he doesn’t release you.

“I don’t-” he starts, choosing his words. “I was honest with you from the beginning about what this was going to be.”

“I know,” you nod. “ _Transactional satisfaction_. I’m not some doe-eyed college kid, I know what we are to each other. But when I’ve experienced something like what you did tonight, I need the connection, too. That was emotionally intense for me, you know that. I think it’s part of what gets you off. So, part of the  _transaction_  needs to be some better aftercare. I don’t like to feel disposable.”

Sam tilts his head, unable to hide the surprise.

“Message received,” he confirms. “For the record, you’re far from disposable. I don’t think I’ve ever met anyone quite like you.”

“Likewise.” You smile as he releases you. You leave your discarded undergarments on the floor, and he’s at your back, ready to zip up your dress.

His hands curl around your hips, pulling you back against him as he dips down to whisper at the shell of your ear. “I want you to touch yourself once when you wake up. And one more time of your choosing before you meet me. Get yourself right to the edge.”

“I will,” you promise softly, eyes shutting as you slip right back into your submissive skin.

“Good girl,” he murmurs, letting his breath tickle your ear. “I’ll see you tomorrow.”


	10. Ten

You sleep until well past noon and when you do wake up it’s to your phone vibrating. You smile, face pressed into the pillow and pick it up expecting a message from Sam but instead it’s Max’s name is scrawled across the screen.

_**Max:** I’m sorry about the other night_

_**Max:** Give me a chance to make it up to you when you get back_

You sigh, putting the phone down and rolling onto your back, staring at the ceiling. The room is still and quiet, there aren’t the busy city noises that you normally hear in your own apartment. As you lie there you think about last night, the way Sam made you feel. Until he came along you would have never considered yourself to be submissive in any sense of the word. Quiet sure, but definitely strong-willed and hard-headed. He’s woken a sleeping giant, a need inside you that’s been aroused and there’s no putting it back to sleep.

Making good on your commitment, you throw back the covers and look down at your naked body, still sleep warm as your nipples harden instantly in the cool air. They’re still sore, throbbing gently the harder they get, a nice reminder of what you went through in the name of pleasure and the lengths you would go to if asked.

One hand slides over your belly and between your legs as you begin to make gentle circles around your clit. Your body responds in an instant, as if all of yesterday’s teasing was just waiting for you pick back up. Your pussy clenches, legs clamping closed for a moment as you moan gently and suck in a deep breath.

You glance at the phone, reminded that several times he’s taken photos of you in compromising positions. You’ve never seen them, but you suspect he’s keeping them for when you’re not together. It’s a thought that gets you even more excited.

Picking up your phone you open the text thread with Keith Campbell and type.

_**Y/N:**  I’m completing my morning task_

_**Y/N:**  Would you like a picture?_

The moment you hit  _send_ you’re second-guessing the boldness of this interaction. He likes to give the orders and perhaps it’s too presumptuous to think he’s concerned about you masturbating in his behalf while he’s making one the biggest deals of his professional career.

It’s only a few minutes later that the phone vibrates again. You take a breath and look at the response, half expecting him to chastise you.

_**Keith Campbell:**  Yes._

_**Keith Campbell:**  Make sure I can see your face and your pussy._

You can’t help but giggle, sorting the logistics of how to fulfill this request. You prop the phone up against the television and sit on the bed with your legs spread, testing the set up before setting the timer and taking nearly a dozen photos of you touching yourself.

The best one looks the most natural, your lips are slightly parted, eyes half shut as you rub your clit. You send it to him and then lie back and finish the task at hand, touching your pussy until you’re right at the edge, sweating and desperate for an orgasm before you stop.

There’s no response, so you get up and dig into your suitcase for a pair of leggings and a sports bra. The hotel has a world class gym and you might as well take advantage while you have the chance.

You’re about to leave the room when he responds.

_**Keith Campbell:**  Perfect_

_**Keith Campbell:**  That wet little pussy is going to be put to good use later_

_**Keith Campbell:**  I won’t be free until the evening._

_**Keith Campbell:**  Come to my room at 9:30. No undergarments._

You stare at the phone trying to think of a smart response and then confirm.

_**Y/N:** Yes, Mr. Campbell_

-

Your excitement is palpable, almost shaking as you approach his room. This feels like the next step. After tonight things will be different, exactly how you’re not sure, but it’s inevitable.

One knock and the door swings open as if he’s been waiting for you. He looks different than you’re used to seeing him. His hair is wet and he’s barefoot in jeans and a plain white undershirt as he steps aside for you to join him.

While you know full well he doesn’t dress in a suit during his personal time, it’s still a shock. He almost looks like a normal person.

“Am I early?” you ask, knowing full well you waited outside his hotel room, watching your phone until 9:30 blinked back at you.

“No.” He looks you over then closing the door. “I’m running late. Our dinner went over and I always have pent up energy after I close a deal. I went to the gym.”

“On time is late,” you parrot his favorite saying, eyes going wide once you realize what you’ve done.

“Indeed.” He smiles, and you’re thankful he’s amused. “You’re the one who was on time and ready to go. You deserve a reward.”

“It went well then?” you inquire, turning to look at him, trying desperately to act like it’s not killing you to make small talk instead of dropping to your knees and offering to suck him off.

“Very well.” He looks at you, eyes shining. “This partnership could take us to the next level. But it’s more money, more responsibility. There’s always give and take.”

He’s silent as you stare at each other, his eyes boring holes into you.

“What did you do with your day?” The question takes you off guard, and you can’t help but grin.  

“I went to the gym, then went out into the city to explore. My phone died and I got lost. I was hoping I’d be able to see the Yoyoi Kusama exhibit but by the time I got there it was too late.”

“The mirrors exhibit?” he asks, stepping closer. “Its coming to Boston isn’t it?”

“Yeah, but only for two weeks and it was sold out before I could get tickets.” You swallow as he gets closer, bare feet padding over the carpet.

“And you completed both tasks I gave you?” Sam shifts the tone of the room with a single question and your cheeks turn red.

“Yes,” you confirm, setting your purse on a small table by the wall. “The first time in my room. The second in the dressing room at Nordstrom. I would have sent you another picture but I was having enough trouble staying quiet.”

“Good.” He steps forward, reaching out to slide a hand along your jaw, his thumb pulling down your lower lip to expose your teeth. He’s done this before and it never fails to make you feel like a prize racehorse up for inspection. “Take your clothes off.”

He wanders over to the couch, taking a seat, watching you disrobe, head tilting as he appraises your breasts, then your stomach and lower.

“How are you feeling after last night?”

“Fine.” You’re completely nude, standing in the middle of the room. “My nipples are sore. It was hard to wear a bra, they’re still a little raw.”

“Do you enjoy that?” He leans back, finger tapping over his knee in thought. “Feeling the after effects the next day?”

“I do. It makes me re-play the things you do to me over and over in my head. I get to relive them all over again,” you confess, watching his throat bob.

“This evening I’m going to start with a spanking,” he explains calmly, patting his thigh. “Come lay here.”

Excitement hums in your veins as you walk to the couch. You look at him, up close and personal as you crawl over his lap and settle down with your ass over his lap. He wedges his hand between your thighs and you spread yourself open as best you can, feeling his finger swipe over your pussy, thumb checking to see how wet you are before he starts.

“How many do you want?” he asks, rubbing an open palm over your butt cheek.

“I-” you hesitate, unsure if this is a test or a genuine question so you throw out the first number that pops into your head. “Twenty.”

“Twenty?” There’s faint surprise in his voice. “I expect you to count out loud.”

And with that his open palm comes down on your ass so hard you shout in surprise, lurching forward.

_Crack. Crack._

Two more follow in rapid succession, nasty slaps that makes your skin sting hot as he rubs his hand over the sore flesh.

“Three,” you wheeze, already breathless as your eyes start to water.

“Stay still,” he corrects as you squirm in his lap, reaching down and holding your upper thigh. “I’ll tie you up if I have to.”

“I’m sorry,” you counter, tensing your muscles.

“Don’t be sorry, do better.” This correction is followed by nearly a dozen hard fast spanks that leave you whimpering into the couch cushion. Both legs are shaking, trembling as you fight through the pain to stay still.

“It hurts,” you sputter, voice ratcheting up an octave.  

“It’s supposed to hurt,” he quips, his hand snaking toward your cunt. “Is it too much?”

“Almost…maybe,” you confess, fingers curling into the fabric of the sofa.

His thumb finds your clit and your eyes roll back into your skull. He rubs you gently, a press over your bud while his other hand massages your ass. You were so concentrated on the pain that you didn’t realize how wet you were, but you can feel it now. The ache between your legs growing as he touches you.

“Better?” He lets up, waiting for your go ahead.

“Yes. Please finish.”

He grunts, shifting under you and you feel his cock straining against his jeans, pressing into your stomach.

He gives you five more solid whacks on your behind and a sixth for good measure, leaving you shaking like a leaf as he sits you up, wiping the corners of your eyes.

“Can I suck your cock?” you ask, the request falling out before you even think about. He gets you so worked up your brain seems to short circuit.

A grin crosses his mouth, as he palms the crotch of his pants.

“Get on your knees,” he instructs. You slink off his lap and onto the carpet as he frees his cock. “Take it all the first time, nice and slow.”

You look up at him, gulping and then slowly swallowing the head of his dick as both hands thread into your hair. It’s a challenge; you normally work up to this, but you don’t stop until he’s lodged in your throat, and you’re drooling around the base of his cock.

“Look at me.” The hands on your hair tighten and you look up, only to find him watching you with his mouth open. “I can see the outline of my cock in your throat, you’re taking me so deep. Just hold it…right there.”

You try to concentrate on suppressing your gag reflex, eyes watering as you groan around his dick. His eyes flutter shut in response.

He tugs on your hair, pulling you off his cock as you gasp for air, spit hanging from your chin.

“Suck,” he commands and you take the head back into your mouth, moaning, feeling your pussy throb between your legs. You lick and suck and stroke him until he’s painfully hard, the swollen crown catching with each pass of your lips.

“That’s enough.” He takes you by the hair again, twisting until there’s a pull at your scalp and you both stand as he pulls you to your feet. “Bend over the bed, spread your legs.”

He guides you to the mattress with a fist full of hair, only releasing so that you can lay belly down across the duvet. Opening your thighs you shiver in excitement.

“Hands over your head.” His instruction is calm and even as you feel him between your thighs, one hand on each leg directly below your butt cheeks.

Reaching up you spread your fingers wide, palms down and wait for what’s to come.

“Beg me for it,” he grits, one hand pressing down on your lower back, the other wrapped around his cock as he drags the head through your folds.

“Please fuck me,” you whine, trying to buck backward. “Please, I want your cock in my pussy. I need it, need to feel you inside me.”

“Your wet little cunt needs this?” He dips the head inside, then pulls back out, rubbing the tip over your clit as you cry out. “How bad?”

“So bad.” You’re utterly desperate now, fingers curling into the bedspread. “I’ll do anything you want. I’ll let you fuck me any way you want to, just please fuck me like this right now. I can’t take it.”

“You feel that ache inside you?” he asks, pressing the head between your lips once again. “Have you ever felt that before?”

“No,” you wheeze, turning your head to the side, eyes squeezed shut. “Never, it hurts, I need you to fuck me. Please, Sam,  _please_.”

He’s quiet and still for a moment and then presses forward, stretching your cunt open as he slides inside in one long thrust. A strained, low mewl escapes your throat, mouth gaping open as he bottoms out and his balls rock into your clit.

“Fuck,” he grunts, hands gripping the meat of each butt cheek. “You’re tight.”

You can’t speak, just whimper as he pulls out and shoves himself back in with a groan. After the maiden thrust, he quickly finds a rhythm, stroking tip to root with each pass. You’ve never felt so full or so stretched, he’s just this side of being too big as you fight to relax.

Sam fills you again and again as you writhe and squirm, desperate to take as much of him as possible. He moves closer, thighs against the edge of the bed and the angle changes, the head of his cock hitting _just right_ deep inside and your clit rubbing the sheets. The pleasure builds fast as you begin to shake unable to control yourself.

“Can I cum?” you beg, unsure of what you’ll do if he says no because this is completely out of your control.

“Of course,” he responds as if you’re asking the silliest question he’s ever heard. “Cum on my cock, let me feel it.”

His permission allows you to relax and enjoy the pleasure, but for only for a moment before you wind up and explode. Your pussy tightens around his thick shaft, desperate pulses, sucking and clutching him deeper as you call out, pressing your face into the bedding with a muffled scream.

Your entire body winds up, goes tight and releases in a flood of relief and ecstasy that’s better than any orgasm you’ve ever had before. Sam doesn’t stop, he just slows down, fucking you through it, rocking steadily until you’re twitching and boneless.

You lay there, limp, wilted on the bed as he takes you by the hips and fucks you with everything he’s got.

“Don’t tell me you’re done already?” He chuckles, breathless as he thrusts into your cunt, the wet smack of your bodies only made louder by the sheen of sweat covering both of you.

“I think you broke me,” you mutter, cheek pressed against the bed.

“You can do better than that.” He slows for a moment, pressing all his weight over you with his cock deep inside.  His hand snakes around your hip and under your belly, middle finger finding your clit.

You jerk the moment he touches you, but there’s nothing you can do to get away, the combined weight of both your bodies keeps his arm pinned in place. You squirm as he rubs lightly over the sensitive bud.

“I can’t-” you pant, squeezing your eyes shut and burying your head face-first into the bed. “I need a break,  _please_.”

“No breaks.” He swats your ass with his free hand and then begins to fuck you again, all while making torturous circles around your clit.

“Sam!” His name comes out a plea, low and long as you squirm underneath him. He’s grinding deep, holding himself inside you with each stroke, before doing it all over again. “Please, please, it’s too much, I can’t cum again.”

“Yes, you can.” He leans down, pressing the side of his face to your temple. “Concentrate on how it feels where I touch, how my cock feels inside you. Breathe slow and steady, stop thinking and _just feel._ ”

Your mouth opens wide, eyes still closed in concentration as you take a deep breath and focus on his finger, slowly moving over your clit. Every other stroke he uses two fingers, pressing on either side and then back to direct contact. He repeats this pattern a dozen times and you’re finally able to come down from your previous high, as he coaxes you toward a new growing pleasure.

His cock is unrelenting, slow even strokes that force you to open up and take all of him in your pussy with every move of his hips.

The pleasure builds on itself, each stroke, every touch bringing you closer and closer to some new finish line. It’s not desperate like the first orgasm, that was fast and explosive from days of teasing and anticipation. This is something deeper, a building thrill that starts between your legs and fans out in all directions.

When you cum the second time there’s no warming. The gradual build stops, then bubbles over as the muscles of your stomach go taught, legs stiffening, neck arching backward. For a moment you can’t breathe, whole body clenching in silent satisfaction, twitching and contracting. The next breath is a desperate sob, pleasure still coursing through you. You howl in desperation, momentarily on another planet. Your mind goes blank, there’s no Sam or job or contract, just the feeling of him filling you and ultimate gratification as you jerk in one final release and go slack.

“Good girl,” he whispers, the warmth of his chest pressing over your back.

He thrusts half a dozen times and holds himself balls deep in your cunt, grunting as he cums, shooting warm and thick in your overworked pussy.  

“ _Fuck_.” He places a hand on your lower back and pulls out. One hand slaps your thighs further apart. Somewhere in the back of your mind, you’re aware that he’s appraising the mess he’s made between your legs, watching his spunk drip out of your cunt.

He’s quiet for a moment and then you feel him flop onto the bed next to you. It’s the better part of ten minutes before you finally open your eyes, turning your head to look at him. He’s watching you as you blink, trying to free your brain from the fog of it all. You’re still pleasure-soaked and dizzy, floating on a high that shouldn’t even exist.

“How do you feel?” he asks, reaching over to push sweat-soaked hair away from your face. The pads of his fingers trail over your temple, then upward sweeping across your forehead.

“Like you drugged me.” You smile wide, looking at his pink cheeks.

“I’m not sure I’ve ever seen anyone cum that hard before.” His voice is soft, and there’s that look again. “You’re beautiful when you cum, it’s like watching someone die and come back to life.”

“That’s sort of what it felt like.” You lie there, watching each other in silence for a long time. His fingers trailing along your hairline, gently stroking across skin, threading into your hair and across your scalp as you practically hum in contentment.

Eventually, his hand falls away, sitting up with a groan. “I’m going to take a shower. You can join me if you want to.”

“Would you prefer I leave now?” you ask, trying to gauge exactly what he wants from this as you roll over and prop yourself up. You appreciate his attention to your request of more thorough aftercare but you also don’t want him to placate you beyond what you need. This is a contractual arrangement after all.

“You can go if you’d like to,” he offers, turning back to face you stark naked in the doorway. “Or you can take a shower and sleep here, with me.”

You try to read his face, but he’s gone stealth again, mouth an even line, eyes staring right through you. You’re about to question this proposition when he beats you to the chase.

“Don’t think for one second that I would offer something that I don’t want or enjoy. I have no desire to bend to anyone else’s needs. If I wanted you to leave, I would tell you to leave. But I’m asking you to stay.”

And with that, he disappears into the bathroom, the shower turns on and you’re left wordless in his bed.


	11. Eleven

You sit there naked as the shower turns on. There’s a part of you that knows you should leave, it’s the safest way to ensure a clean division between sex and, well, everything else. But the truth is all the logic in the world doesn’t stop you from getting up and joining him in the shower.

He turns toward you as you open the glass door and step inside, his hair slicked back. He moves out of the way for you to wet your hair before switching places. He doesn’t touch you, instead he watches as you lather your body with the hotel provided soap. His eyes follow as soapy hands move between your legs, then over your breasts. He waits for you to finish and then steps out, wrapping himself in a fluffy white towel, handing one to you before wordlessly disappearing back into the room.

You follow him, toweling dry, trying to act casual as he stands stark naked, rubbing his hair with the towel and slipping into bed. You do the same, walking to the other side and crawling under the sheets as he reaches over and turns off the light.

“Good night,” are his last words as he turns onto his side, facing away from you and settles in.

-

There’s a hand rubbing up and down your back as you lie belly down, still in the depths of sleep. Slowly you blink awake, the early morning sun shining through a crack in the curtains, cutting like a knife through butter into the dark of the room.

While you don’t know what time it is, it’s still early enough that no part of you wants to move. It’s Sam’s voice that brings you back into the land of the living and the realization that you’re still in his bed.

“You have to get up.” A big, warm hand spreads wide across your back, fingers fanning out. The feeling of his hands on you, skin on skin is a simple but rare pleasure.“It’s almost six and Pepper will be here soon. Our flight leaves at nine, and you need to pack.”

“It’s too early, just leave me here. I’ll live on the West Coast now.” you whisper, rolling onto your back. He’s hovering above you, propped up on one elbow looking bright eyed at this ungodly hour. “Do you ever sleep?”

“Rarely.” He pushes a strand of hair back from your cheek. “Really, you need to get up.”

“I’m moving.” With a final push, you force yourself to sit up and get out of bed. You’re naked and it’s cold as you hop around the room, trying to find your clothes and get dressed. Still half asleep you walk to the door in a daze and he follows you. “Last night was…incredible. Really, I’ve never felt anything like that.”

He seems to enjoy your early morning confession, grinning as you yawn into the back of your hand.

“Go on,” he opens the door. “You can sleep on the plane, you deserve it.”

 

**Five Days Later - Tuesday**

You’ve spent the better part of two days staring at lists of phone numbers and calls. The computer does most of the cross-referencing, all you’re left with is a spreadsheet full of names, dates and times. Thousand of them.

It’s early afternoon when you realize that something’s wrong.

Before you were assigned to the endless pit of phone calls, Max had you sorting through and categorizing depositions, ensuring the transcriptions were correct. You know this case inside and out. You’ve heard every word of testimony a dozen times and that’s how you know that Kurt Jablonski, your client, swore up and down multiple times that he never made direct contact with a private investigator named Lea Hammond.

And yet here you are staring at a number identified as one of Lea Hammond’s burner phones making and receiving calls from an office line that only Kurt had access too. His calls are normally made through his security so it’s possible he’s naive enough to think that there wouldn’t be a trace, but you’re staring at the proof of their connection.

You’ve got no idea what this means, but it’s a huge case. Sam’s had teams flying back and forth from Florida for months.

Now comes the hard part, you have to tell Max.

You never returned his texts and he’s been giving you the cold shoulder. But you report to him, at least for this case, so there’s no way around it. You write down the names and dates on a post-it and head to the conference room where Max has set up shop with half a dozen other junior associates.

“Excuse me,” you knock lightly on the door frame and they all look up. Frank Walenchecz looks from you to Max and grins, which piques your interest but that’s not why you’re here. “Max, can I talk to you for a minute?”

“We’re kinda in the middle of something here.” He rotates his chair, eyeing you up and down. “I’ll find you later if you need me.”

Everyone in the room chuckles and your cheeks flush hot.

“I think you should look at this, I found something-”

“I said we’re busy.” He’s emboldened now, his condescending tone laced with an underlying hostility that you pick up on in a second.

“Max, this is serious,” you insist. “It says on the schedule that the team in Florida is going through final prep with Mr. Jablonski but-”

“Why don’t you worry about your filing and leave the thinking to the big boys, huh?” He tilts his head, making no attempt to hide as he stares at your breasts. “I’ll find you later, sweetheart.”

You can hear snickers as you shut the door, humiliated.

You wait. And wait.

It’s nearly six when you walk back down the hall only to find the conference room empty. He’s left for the day.

 

**Wednesday**

You’ve only been in the office for an hour, sorting through a new stack of documents when Lance Barton saunters up to your desk. He’s not exactly a friend, but the two of you are friendly per se. He’s a junior associate and just as full of himself as every other lawyer working at W & S, they all know how good they have it.

“Good morning,” he perches on your desk, shoving a paperweight to the side to make room for his ass.

“Hey,” you look at him, offering a genuine smile. He doesn’t say anything, just sits there staring at you with a shit eating grin on his face. “Did you need something?”

“Actually, I came to ask you that.” He chuckles, biting his bottom lip. It takes you a minute to understand exactly what he’s implying. When the realization finally dawns you’re so taken off guard that you don’t know how to respond.

“I-” you start, sitting back, staring at him in disbelief. “I’m not sure I understand what you mean.”

You turn back to your work, trying to ignore him, but he doesn’t move.

“Come on,” Lance leans down, placing his hand over yours on the desk, you jerk it back in response, unprepared for actual physical interaction. “We’ve always gotten along, haven’t we?”

“Please stop.” You pull your hand away, clutching it in your lap.

“Max said you liked to play hard to get.” He whispers, now close enough that you can feel his breath on your cheek. “But he also said it was worth it, that you’re a wild little thing.”

You look at him wide-eyed, mouth falling open as nausea sets in. “Max told you that?”

“Don’t be shy.” Lance smiles, his eyes trailing down your body. “You just let me know the next time you need an itch scratched and I’ll take care of you.”

He saunters away, looking smug, leaving you gutted. You’d already guessed from Max’s reaction yesterday that he’d greatly exaggerated his relationship with you, but this is a whole other level.

Greg Smith from IT walks by your desk, eyes lingering too long and you know it has already grown into something you’re not going to be able to control.

 

**Thursday**

“Everyone knows your dirty little secret.” Pepper pours herself a coffee looking up at you. “I mean, you probably think you’re hiding it but I can see right through you.”

You almost choke on your spit, stopping to stare at her, swallowing hard.

“What are you talking about?” you stammer and she smirks, sipping her coffee.

“Oh stop it. The whole office knows about you two.” She shakes her head and you want to melt into the floor.

“You’re talking about….Max?” 

_God, you hope it’s only Max._

“Who else?” Pepper is always a bitch but she’s really enjoying this. “I knew there was something between the two of you.”

“There was and never has been anything going on between us.” You correct her, holding your head high.

“I could have told you he was a snake. They’re all wannabes with too much money who think they’re going to be Sam Winchester some day. It’s pathetic.”

“Whatever he said, it’s not true.” You want to ask for more details but you’re not sure you could handle it.

“He told everyone, might as well have sent out a newsletter. Every nasty detail, how you suck cock, how you begged him to fuck you… _everywhere_. He told Colin you’re too slutty for him. Too much of a whore for Max…that must be a new low.”

“Why are you telling me this?” you whisper, fighting back tears. There’s a swell of anger and humiliation rising in your chest.

“Because you should know. I might be a lot of things, but I’m not afraid to say things to someone’s face. I know you’re Sam’s favorite right now, God only knows why. But that doesn’t mean anything in the real world. Outside of his office, you’re just a small fish, fighting for room in the pond with the rest of us.”

She turns on her heels and walks away, leaving you stunned.

-

The last thing you want to do is see Max face to face, but you need to show him the information you found. While you’d love to see him crash and burn, it could affect Sam and you won’t let that happen.

You knock twice on the door to his small, windowless office and he looks up. His face hardens when he realizes it’s you. “Back for more? Can’t stay away huh?”

“What are you talking about?” You shrug, stepping inside and shutting the door. “It’s just us now, stop the act. I thought we were friends, Max. Why are you doing this?”

“What am I doing?” he asks, picking up a stress ball and squeezing it in his fist. “I haven’t  talked to you in a week.”

“You’ve talked to everyone else. Telling stories about things that never happened.” Stepping closer to his desk you search his face for some kind of understand. You didn’t see this coming. Are you this bad of a judge of character? “Why are you trying to hurt me?”

“Why are you such a cock tease?” he spits, crushing the foam ball in his grasp.

“You know,” you back out the room, defeated, “the sad part is that I thought you were a good guy.”

“Why don’t you go find someone else to play your games with,” Max calls out as you leave and you hear the ball hit the wall with a soft thump.

 

**Friday Morning**

Sam waits outside the door to the conference room as Pepper hands him the latest update on the case. He opens the folio, reading through the documents. He’s always fully prepared.

“Do you need me?” Pepper asks, “Because I need to finish the notes from your call with Mr. Takahashi. You’ll need the final proposal before your one o’clock.”

“No,” Sam shakes his head without look up. “I should be back in my office by eleven. We’ll have time to review.”

She wanders off and Sam’s flips through page after page, scanning the notes. He’s not really listening, it’s your name that pulls him out of what he’s reading, moving closer to the open door.

“ _I’m telling she was practically begging for it,_ ” Max explains.

“ _If Y/N was so into it then why are you so hot and cold?_ ” Another voice asks. “ _You’ve been after her for months._ ”

“ _Because every other guy has already been there._ ” Max laughs. “ _I mean she’s a real whore, let me fuck her ass the first time. That’s how you know she’s been open for business._ ”

“ _Shit,_ ” someone else grunts. “ _If you don’t want her, I’ll damn sure get in line._ ”

“ _Go for it man, two drinks and she was all over my dick like she hadn’t been fucked in years. She was starving for it._ ”

 

**Friday Afternoon**

“What is it?” Sam snips, looking for up for only a second. You haven’t seen him since you got off the plane in Boston last week. You know he’s been busy but you expected less hostility.

“I need to show you something.” You inch into his office.

“Can it wait?” He sits up, pulling off his glasses to stare you. He normally looks you up and down but right now his eyes are boring a hole into yours with an unwavering stare. “I’m busy. I don’t have time for you today.”

_Jesus._

You take a breath, holding back with everything you have, you’ve wanted to cry for forty-eight hours but you didn’t think Sam would be the one to push you over the edge.

“Um-” you stutter, words getting caught in your throat.

“ _Um_?” He raises an eyebrow. “Pull yourself together, use words like an adult.”

You swallow hard, tears brimming, as you try to swallow the thump in your throat.

“There’s something I came across when I was sorting through phone records for the Jablonski case.” You manage stable words, masking your looming breakdown.

“And you’re bothering me with this why?” He asks plainly as if you’re some low-level employee he’s never laid eyes on before.

“I just thought-”

“What did you just think? That because I fucked you I would suddenly have time for whatever this is?” His eyes are on fire and you wished you could melt into the floor.

“Jesus Christ, you’re a real dick, you know that?” you whisper, a tear running down your cheek, mouth trembling. “What did I do?”

His eyes light up, rage threatening right there under the surface. “Why aren’t you giving this to your project leader? Max has time for you, I’m sure.”

“I tried. He won’t listen to me.”

“Why?” Sam’s jaw locks, seething with anger. You’ve got no idea where this is coming from but you’re fully prepared to leave this building and never come back. “Stop crying, it’s pathetic.”

“Because,” you close your eyes, fresh tears falling, you’re really crying now. You stare at the floor, unable to take any more of his glare. “Because he’s mad at me.”

“Why is he mad at you?” He pushes as if he’s waiting for some lurid confession.

“I wouldn’t sleep with him. He’s been an absolute asshole. He’s successfully made my life a living hell. I’m pretty sure he told everyone in the building that I’m a whore. I’ve got people I don’t even know whispering about me in the halls. I tried to show him but he won’t listen to me. I found something. I think it’s important so I came up here to tell you and now you’re…whatever this is. Please just take this so I can leave.”

You hold out a folder, wincing as he steps forward. He takes the folder out of your hands, but the next thing you feel is both his hands cupping your face, thumbs pressed into your cheeks.

“Calm down.” His voice is softer now, less commanding, more soothing.

You look at him, and gone is his threatening stare, it’s been replaced by something gentler.

“I haven’t done anything, to anyone.” you offer, stripped bare of pretense as you look up at him. “I’m just trying to help.”

“I jumped to some conclusions, I shouldn’t have spoken to you like that.” It makes sense now, he’s heard the rumors. One of his hands moves from your face to your chest, placing his hand wide over your heart, resting between your breasts, guiding your breath. “I’m sorry.”

While it doesn’t excuse his actions you’re fairly sure Sam Winchester rarely apologizes, if ever.

“Okay,” you whisper, unable to dive any deeper, not right now at least.

“I’ll look through what you brought and take care of the Max situation.”

“I’m not a snitch,” you gulp, “I didn’t tell you to get him in trouble.”

“I know that. But you  _did_ tell me and I can’t have one of my employees talking about another like this. I won’t allow this kind of hostile environment for anyone.”

“He’s going to know I told you.”

“He’s going to know you told HR, because that’s how we’ll deal with it.” He sets the folder on his desk and picks up his phone.

“You’re done for the week. Go downstairs, I’ll have my driver take you to my house. You’re going to spend the weekend with me.”

“The weekend?” You look up, wiping tears as your mind tries to shift off of Max and into whatever this new territory is. “I don’t have anything with me.”

“You won’t need much.”

-

Sam’s house is a huge, modern home in Newton, Massachusetts. You know from listening to Pepper that he has a loft in Boston but this sprawling architectural wonder is his real home, far outside the city.

Dealing with him on a more intimate level it’s been easy to forget that he’s filthy fucking rich. He’s made more money than most people can dream of and this house is a jarring reminder that you’re in his world now.

The driver walks you to the door, punches in a code and ensures you’re inside before leaving. The floors are dark wood and everything else is stark white, it makes the place feel almost antiseptic. You take your shoes off and trail down the hallway that opens up into a generous living area, twice the size of your entire apartment. There is a couch, several chairs, and a coffee table. The walls are bare, save for one huge painting hanging on the wall, it’s all dark colors and strange shapes.

You continue exploring, wandering down a narrow hall to the right and find the kitchen. It’s just as devoid of personality as the rest of the house. He could feed a small army and you wonder if he’s ever lonely being one man with all this unnecessary space.

There’s a labyrinth of empty bedrooms, filled with furniture and not much else. At the end of this hall is his room, it’s unmistakable. In contrast to the rest of the place, there are splashes of color. The door to his closet is open and you slip inside, flipping on the light to find hundreds of suits, pressed and hung with meticulous care. There’s a second closet filled with his casual clothing, sneakers, and gym clothes. It sparks a lot of thought about what he’s truly like outside of the professional world.

Is this it? Is all this naked space his life? It seems…unfulfilling.

At the end of the closet, there’s a dresser with two pictures sitting on top. You pick one up and examine it. It’s a family, mother, and father, a young boy and a baby. It’s easy to guess that the baby is Sam, this was a life that was taken from him.

The second photo is unmistakably Sam with a mop of wild hair hanging over his forehead. He looks to be in his early twenties and he’s smiling bright and happy, eyes lit up with joy. He’s got his arm around a beautiful blonde who’s pressing her lips to his cheek. This Sam looks alive, warm and inviting. Another version of him from a happier time.

There’s a faint sound and you set the picture down, shutting off the light and scrambling out of the room. You find him in the living room, slipping his suit jacket off and laying it over the back of a chair. He looks up, a half-smile crossing his lips.

“You,” he points to you, shaking his head. “Just saved me from an utter disaster. I have twenty lawyers on that case, five paralegals and you’re the only who caught the phone calls.”

“It was something?” you question, moving closer.

“More than _something_. Kurt hasn’t been telling us the truth. If we had moved forward with our current strategy he would have ended up in jail and our reputation would have taken a massive hit.”

“Well, I’m glad I could help,” you offer, still reeling from the rollercoaster of a day you’ve had. “Before you say anything else, there’s something I need to say.”

“What is it?” he asks, getting closer.

“I know you have a lot going on. You’re busy and you don’t always have time for me. I understand that you’re blunt and like to get right to the point. But I can’t handle the way you spoke to me today. I enjoy what we have, but I won’t be around someone who treats me like that.”

He waits for a beat, eyes honing in on you, his head tilting as his tongue darts out. You can practically see the gears turning.

“I overheard a rumor and took it as truth. I, of all people, should know better,” he offers. “I don’t share. I’ve never played well with others and when I heard what I did, I reacted. I am sorry for that. I asked you to trust me and I need to trust you in return. It’s the only way this works. I trust you to keep your word, make good on your commitments. I will never speak to you that way again.”

“Good.” You gulp, feeling suddenly small in his living room. “Let’s not talk about it anymore.”

“Agreed.” He moves past you, reaching out to squeeze your arm as he heads off toward the kitchen and you follow. “Are you hungry?”

“Yea - Yes. I am. I was so worked up all day, I haven’t eaten anything since last night,” you confess, almost afraid of what kind of strange, kale-infused delicacy he’ll offer you.

“I’ll make something.” He opens the refrigerator, looking back you. “How do you feel about beets?”

-

“What I’m about to do is all about trust,” Sam explains as you sit naked in his lap, knees on either side of his thighs. His cock is thick and hard, trapped between your bellies.

“I know,” you nod, one hand on each of his shoulders. Your nails sink into his skin, holding on like he’s already begun. You look him in the eyes, searching for understanding. “I trust you, I’m just…nervous.”

“You’ll like it.” He nods, both hands holding your hips tightly. “It’s an incredible release.”

His hand wedges between your bodies again, finding your clit, rubbing a few last times before he gets started. He’s spent the better part of an hour getting you worked up, you’re wet and throbbing, ready for more.  

“Lift up,” he instructs and you rise up on your knees as he takes his cock into his hand and slips the head into your pussy. “Now lower down, take it all.”

You stare at him as you slide down his dick, not stopping until you’re filled to the brim.

“Jesus,” you gasp, eyes fluttering closed for a moment. He’s thick, a wonderful stretch that sends little jolts of pleasure up your spine.

“Hands behind your back.”

You comply, placing your wrists together at the base of your spine. He picks up his discarded tie, reaching around and securing your wrists. The fact that he doesn’t need to see to be able to properly tie you up, has you both excited and concerned.

Sitting back he looks at you, then down to where you’re sitting on his dick.

“Fuck yourself on my cock, slowly.”

Lifting up you hum with satisfaction, feeling the drag of him inside you. It’s only intensified when you sink back and find a rhythm, even and constant, as you stare at each other. After a few minutes he starts to breath faster, mouth clamped shut as he studies your face. One hand comes up and slides around your throat. His fingers nearly reach the back of your neck, thumb pressing into the opposite side under your jaw.  

He squeezes, not hard, just enough to make you feel the pressure and you whimper, sliding up and down his shaft. Leaning all the way back in the chair, he reaches between your bodies with his free hand and begins to carefully rub your clit.

Your mouth falls open as the pleasure builds, everything between your legs slick and throbbing. His cock alone would be enough to get you off like this, you’re not used to the stretch yet, you doubt you ever will be, but it’s a wonderful challenge as you lift yourself up and down in his lap.

“Feels so good,” you whisper, biting your lower lip, his thumb moving faster over your swollen clit.

“Stick your tongue out,” he instructs. You blink, feeling the all too familiar shame creep in as you drop your jaw and stick your tongue out.

He keeps you just like this as the minutes tick by, your whimpers and moans sound even more desperate with your mouth wide open, tongue hanging out like some kind of slutty porn star.

Tugging at your hands you almost falter, only to have the hand around your throat grow tighter, holding you in place.

“You don’t have to ask permission to cum, just let it happen.” And with that his lips curl and his fingers clench and suddenly you can’t breathe. You knew this was coming, he’d prepared you for it but the first time you can’t help the panic, your heart speeding up.

For five seconds you are open-mouthed, fighting for air and then he lets up and you suck in a huge breath.

“Don’t stop fucking,” he reminds you. You’ve slowed down but you pick up the pace, sliding back and forth more than up and down. “Tongue back out.”

You comply and his grip tightens until you can’t breathe again and this time it’s longer. His thumb works faster over your bud, his hips rise up, keeping his cock moving inside you.

This time it’s ten seconds, and by the time he lets go your whole body is hot, sweat breaking out from head to toe.

You expected more pleasure, it’s not exactly bad but also not the pay off you anticipated.

After a few deep breaths, you stick out your tongue and ride him as his fist closes around your throat, tighter than the two previous times. His thumb presses firm, you feel your orgasm building as he squeezes the last breath out of you. You start to squirm, pulling at the restraints out of instinct. A desperate gagging sound leaves your throat and you’re getting closer and closer and then it happens at the same time. Your vision starts to go spotty and you cum at the same time. He eases up, but barely, still controlling the air supply as you jerk on his cock.

You’re floating and then there’s a rush of pure euphoria. It’s a tingling, weightless feeling that seamlessly melts into the pleasure of your orgasm and the whole world fades away. There’s nothing else, only the feeling of your body rolling up and down and an incredible pleasure between your legs.

Unsure how long you’ve hung in this transcendental state, you blink, vision clearing only to find Sam staring at you, both his hands cupped around your cheeks, holding your head up.

“Wow,” you whisper smiling like a fool, looking at him from under hooded eyes as an overwhelming wave of satisfaction and bliss sets in. “Thank you.”

“It looked incredible.” His eyes are lit up and moving quickly, searching your face.

“Untie me please,” you request softly, not entirely of sound mind yet.

He blinks, hesitates for a moment, then one hand leaves your face to reach behind you to free your wrists. Without thinking you wrap yourself around him, both hands sliding behind his neck as you rest your head on his shoulder.

His palms slide up your back, holding you as you come back down to earth, thumbs stroking back and forth until your breathing is back to normal. Once you’ve semi-recovered you sit up, inches away from his face as you look at each other. He’s even more handsome up close, the little wrinkles around his eyes and the pink of his lips are beautiful.

Wordlessly you lift yourself up, letting his cock slide almost of your pussy before sinking back down, finding a pace that makes your thighs burn as you ride him, desperate to give him the same release he’s just gifted you.

“Fuck,” he groans, head tipped back, the muscles of his neck straining. The two big hands on your hips pull you down onto him, holding you in place as he cums, spurting warm inside you until he’s finished.

After a few minutes, he lifts you up and off his semi-hard cock, rubbing his knuckles directly over your cheek, a tender caress that makes your eyes close in response.

“Now, get on your knees and suck my cock until it’s clean.”

-

“Sam,” you start, watching the subtitles on the muted TV as a newscaster talks about the upcoming election. “Why am I here?”

“What do you mean?” he responds, only half paying attention.

“I’m in your house, in your bed. You said you want to me stay all weekend. Don’t get me wrong, I want to be here, but I didn’t think you would want someone in your personal space.”

“I don’t mind having you in my personal space as long as it’s at my request.” He explains evenly, glancing up. “I’ve been busy this last week. My schedule is only going to get tighter. Weekends might be the only time we get to see each for a while. I won’t have time for the same interactions while I’m at work.”

“That makes sense.”

“Are you alright with that? Do you have a cat that needs to be fed?”

“No, no animals, no social life to speak of. We’re perfect for each other.” You smile and he grins looking back to the screen.

“What will happen to Max?” you ask, laying on your back staring at the ceiling of his bedroom.

“Do you care?”

“No. I’m sure he deserves whatever he gets,” you nod, the feeling of the last few days washing over you again.

“What happened to make him so upset?” Sam’s inquiry seems genuine.

“I turned him down. Some men are like that, for whatever reason they can’t handle being told no. Honestly, I had no idea he was that upset with me. I can only imagine what they all think of me. It’s so embarrassing.”

“You’re not the one that has anything to be embarrassed about.” His eyes go back the report in front of him, sliding the screen up but still talking. “Even if everything he said was true, it shouldn’t matter.”

He goes back to his work, reviewing some document that can’t wait until Monday and you lie there, pretending to watch a rerun of Frasier that comes on after the news broadcast.

“Sam, can I ask you something?”

“It seems like you’re going to regardless of my answer.” He glances at you.

“Are you happy?”

He stops, looking up and forward before turning to staring at you as if you’ve just asked him to hop on one foot.

“Is anyone?”

“I am.” You roll onto your side. “I mean, I’m not over the moon every day, but I’m content and I have moments of real, true happiness.”

“Why are you asking me this?”

“I was just thinking about you. I’m sorry if I shouldn’t have asked-”

“It’s fine.” He sets down the tablet on the nightstand and rolls onto his side, propping his elbow on the pillow. “No, I’m not happy in a traditional sense. I’m satisfied. I’m focused, I accomplish things no one else would ever be able to. There are a lot of things you have to give up to have the career I’ve had. I built something. I gave up happiness for success, it was a conscious choice.”

“Don’t you want more than your job?”

“No.” He shakes his head without hesitation. “When you add too much into the mix, things get messy.”

“Is that why you have me? I mean, you’re a pretty big deal. I can’t imagine you’re desperate for dates.”

“I don’t date, I have no desire for that. Having people in your life makes you unfocused, they’re distractions.”

“I’m not a distraction?” you inquire. A psychologist would have a field day with him.

“You are exactly what I need you to be. I’m not a robot. I have the same base urges as every other red-blooded American male, but instead of marrying the first pretty girl with long legs that liked my money, I decided to leave sex in its own category. My life is compartmentalized, things run smoother that way.”

“Do you have friends?”

“Not anymore.” His voices wavers, just a little but you catch it, trying your best to not let on. “For me friends are either a liability or a disappointment. I’ve never met anyone who didn’t fall into one of the two categories.”

“Geez, which one am I?”

“You’re not my friend,” he states, eyes narrowing. “You are a category all your own.”

“I’m not sure if that’s a good thing.”


	12. Twelve

You spend the weekend naked and fucking in nearly every room of his house. Sucking his cock in the middle of the kitchen, laid out over his sofa on display while he reads the paper, spanked until your ass is bright red. By Sunday night you’re tied to his bed frame and looking forward to the work week so you can get a few nights of well-deserved rest. It’s almost midnight when he sends you home, patting your cheek in appreciation then standing in his doorway, watching as you walk toward the waiting car. 

There are faint black and blue marks around your wrists, leftover reminders of being bound and gagged. You look out the window, pressing on one wrist and enjoying the fading pain as the moment comes back in vivid detail. Sam can make your body respond, even when he’s not there. 

There a question flickering to life in the back of your mind  - how long can this last? But you push it down, refusing to acknowledge it. 

 

**Five Months Later**

“What is going on down there?” Rolling your chair back, you glance down the hallway. 

“Brent is getting axed.” Millie wheels her chair toward you, and the two of you sit side by side listening to the commotion down the hallway. There’s muted yelling coming from one of the conference rooms. 

“Really?” You know he screwed up, it was bad enough for Sam to bring up in casual conversation. “I liked Brent, he wasn’t a total ass like the rest of them.”

“That’s probably why he didn’t last,” Lexi chimes in, walking up behind you, resting her hip on the corner of your desk. “I heard he got called up to the attic this morning. Word is, he told Sam that it wasn’t even him that mixed up the dates, it was Tobias but they blamed him.”

“You think that’s true?” you ask, listening as the yelling escalates and two uniformed security guards come trotting down the hallway. 

“I don’t think Sam Winchester does anything unless he’s one hundred percent sure about it.” Millie offers and you shift in your seat. 

While your arrangement with Sam has grown into itself, it still makes you uncomfortable when anyone else talks about him. It feels like they’re going to find out your secret just by the look on your face. 

Life has been split into two categories. The normal work week, which is usually boring and predictable - you go to work, go home. You get the occasional text from Keith Campbell, a little homework every now and then but for the most part your professional life has turned into just that, strictly professional. 

It’s the weekends that you indulge in each other. From Friday afternoon until Sunday night you live in a sexual fantasy, engaging in whatever wonderful torture he decides to inflict. He was the one who talked of compartmentalizing his life but you’ve done the same. 

_Bang._

The door to the conference room flies open, hitting the wall with a thud. All three of you jump. Brent is hauled out of the room by the guards, who are now joined by four more, as they wrestle him out of the building. 

“Poor guy,” you mumble, looking away. 

“Another one bites the dust.” Millie shakes her head. “We’ve got it good. We stay under the radar and just do our job.”

“We should head over to the auditorium.” Lexi taps the back of your chair.

It’s Sam’s monthly employee meeting and everyone is expected to be in attendance. Grabbing your coat, the three of you head out of the main building to the staff auditorium. There are always refreshments and snacks if you get there in enough time and you wander around, talking to other employees and sipping seltzer. 

You’re discussing Lexi’s upcoming blind date when there’s a tap on your shoulder. Turning, you find Pepper, looking as irritated as always. “He wants to see you. Now.”

Sam hasn’t called for you in person, during work hours, in months. You’re taken off guard, looking sideways at Millie and Lexi who are both as surprised as you are. You’ve done your best to keep the fact that you occasionally meet with him a secret. As far they know you’re just another low-level assistant 

“Come on!” Pepper snips, grabbing your arm and hauling you off. You follow her backstage, winding through a labyrinth of hallways until she stops at the door to a small room. You step inside and she closes the door. 

Sam is standing, one hand in his pocket eyes fixed on his phone. He looks up, smiling when he sees you. “Hello.”

“Hi.” You clasp your hands together. 

“You look surprised. Am I interrupting something?” He cocks an eyebrow, stepping closer. Every action he makes has a purpose, especially the way he moves. 

“Not at all.” You tilt your chin up toward him. “I was just caught off guard. You don’t mix work and _us_ these days. I’m always happy to come when you want me.”

That last statement makes his eye twitch, nostrils flaring. 

“I’m glad to hear it.” He inches nearer, eyes dropping down your body. “I wanted to make sure that you don’t have plans this weekend.”

“Do I ever have plans?” you counter, watching him lick his lips. You know one thing for sure, the longer this has gone on, the hungrier he is for you. And the feeling is mutual. 

“Yes, but today is your birthday. People normally celebrate with friends. You don’t have anyone coming into town?”

“No,” you nod, holding your head high. “I’m all yours.”

“Good. Be ready tonight at eight. Wear a dress, something nice. I’ll pick you up.”

“We’re going out?” 

He hasn’t taken you anywhere other than his bed since San Francisco. In fact, some weekends you never wear anything at all, naked from Friday to Sunday. You wonder if this is for your birthday or one of his social engagements. It’s not uncommon for him to take a date, but as far as you know it’s always Pepper who accompanies him in public. He says it’s _cleaner_ that way. Everyone knows she’s his assistant so there are no misunderstandings. 

“Yes,” he confirms. “No panties, hair down.” His eyes linger then he steps back, smoothing down his tie. 

“I look forward to it.” You watch as he leaves the room, always left in a wake of excitement and expectation. 

-

It’s almost eight as you look in the mirror, adjusting your dress. It’s black and tight, falling just above your knee. The neckline is lower than you're used to but nothing scandalous. It’s the back that’s the real show stopper, it’s open all the way down to just above your ass crack. You hope it’s not too much, Sam will occasionally comment on your clothing choices but you think you’ve got a handle on his taste. Above all else he prefers class. 

His car pulls up just before eight. You’re waiting by the front door of your brownstone apartment building, hurrying down the steps, eager to find out what’s in store. 

The driver opens the door and you slide in next to him. 

“How are you tonight?” he asks, his hand already on your knee, slipping between your legs. 

“Excited. I haven’t been out in a long time.” 

“Well, let’s hope this evening lives up to your expectations,” he purrs, hand sliding just a little further up your leg. “I hope you’re not too hungry, we aren’t eating until after.”

“After what?” You look up, his fingers pressing into the warm flesh inside of your thigh. 

“You’ll just have to wait and see.” He grins, giving you a squeeze and removing his hand. “Before we go any further, I need to tell you that I allowed Pepper to choose a second assistant for the Tokyo trip next month. I expressed my preference for you, but she chose Lexi.”

“That’s no surprise I guess.” You can’t help but be disappointed. “I mean, I’d like to see Japan, but you know better than anyone Pepper hates me. We don’t work well together.”

He chuckles. “She’s not one to hide her feelings.” 

“How long will you be gone for?”

“Two weeks. Don’t worry, I’ll have you report to me every night. You’ll have a list of tasks for while I’m gone.” He holds his stare and you get lost in the moment, drowning in those eyes that you’ve come to know oh so well. 

“I look forward to it.”

“I would expect nothing less. We’re here.” He points out the window as the car pulls up to the Boston Museum of Modern Art. 

“We’re going here?” you ask looking back at him. “It’s closed.”

“Not to us,” Sam corrects you, allowing the driver to help you out before following. You feel his hand on your naked back, sliding down to the dip in your lower back. He leans down to whisper in your ear. “Excellent choice.”

“I thought you might like it.” You smile, taking his arm and walking toward the entrance. The thought dawns on you like a bolt of lightning. “This is the Yayoi exhibit.”

“You said you wanted to see it didn’t you? The timing was perfect.” He looks proud of himself as a porter opens the front door for you. 

“I said I wanted tickets-” You’re dumbfounded, looking around at the empty museum. 

“This is better. A private viewing without the distractions.” 

There’s a man bustling toward you with several people following. 

“Mr. Winchester!” A short, sharply dressed man extends his hand. “We are so honored to have you here. I’m Cecil Baton, the general director. On behalf of the entire board, we want to extend our heartfelt thanks for all the support you’ve offered over the years.”

“It’s my pleasure.” Sam nods in confirmation, slipping an arm around your waist to pull you forward.  “This is Y/N, she’s very much looking forward to seeing Infinity Mirrors.”

Cecil takes your hand, shaking it vigorously. 

“We are thrilled to be able to repay your generosity by hosting a viewing for you and your lovely friend.” Cecil makes a _tsk_ ing sound and a uniformed waiter steps forward with two flutes of champagne. “May we interest you in a glass of Dom Perignon?”

“Thank you for the gesture, I don’t drink,” Sam affirms and looks to you. “Go ahead.”

You hesitate for a moment before taking the glass off the tray and then the two of you are whisked down a hall, as you explore the wonders of each colorful, unique room. 

By the time you’re done, you’ve finished three glasses of champagne and are floating on cloud nine as Cecil chatters away, walking you out. He goes on and on about how wonderful Sam is. Leaving you to ponder exactly how much money he must have donated to get a reception like this. You probably don’t want to know. 

“What did you think?” he inquires as you walk back toward the car. 

“It was...better than I could have imagined. What an experience.” You feel like you’re vibrating with happiness. While you’ve never lived through any kind of cruelty, you’ve also never been pampered in any sense of the word. This is a scenario you could never have imagined. You turn to him, stopping in your tracks and gripping both his arms. “Thank you so, _so_ much.” 

“It was nothing.” He shakes it off, giving your elbow a squeeze. “Come on, we’ll be late for dinner.” 

-

Dinner is at a French restaurant called Mistral. 

He orders for you, but he’s better at it now than he was in the beginning. He’s come to know your preferences, even ordering you a fourth glass of champagne, toasting you with his seltzer water. 

“Sam,” you start, looking from the tuna tartar. “Is there a reason you haven’t touched me yet tonight?”

“I touched you in the car,” he smirks. 

“Yes, but you didn’t _touch_ me. I mean, you are going to, aren’t you?”

“Don’t worry,” he chuckles, sitting back in his seat, one arm resting on the table. “It’s your birthday. The one day of the year I’m going to leave it up to you. Start thinking about what you want tonight. It’s your choice.”

You can’t help your grin, giggling a little as you sip from the flute. “I’m not sure I even know where to start.”

“I’m sure you’ll think of something.” With a genuine laugh, he goes back to his salad as you talk about your favorite part of the exhibit and the various other artists you hope to see in your lifetime. When you finish he’s quietly watching you, seemingly satisfied to sit and listen as you ramble on. “Do you have anything on your bucket list? I know you have more money than God, so you can probably see and do anything you want but there’s gotta be something.” 

“Hmm,” he indulges your question, really giving it thought. “I want to see the northern lights. I’ve never had the chance.”

“That’s a good one,” you agree as your empty plate is swapped out for a giant tower of chocolate and raspberries. You almost squeal, a little tipsy and having arguably the best birthday of your life. “Come on, try some. One spoonful of sugar won’t kill you.”

“No.” He shakes his head, face lit up in amusement. 

“Oh come on Sam, it’s my birthday. You said I’m in charge tonight...one bite.” 

He contemplates your request and just when you think he’s going to tell you _no_ he reaches over and spoons a bite of your dessert. Popping it in his mouth and wincing, “too sugary.”

“Your loss,” you laugh, digging in. 

-

“Have you decided?” Sam's teasing, watching you blush in the low light of his bedroom. 

“Yes,” you nod. “There are several things I’d like tonight, but first I want you to take your clothes off.”

He raises his eyebrows, but compiles immediately, toeing his shoes off and reaching for the buttons on his shirt. You do the same, stripping down until you’re both nude and staring at each other. He’s already half hard, cock thickening right before your eyes. 

“In a little bit, I want to suck your cock. Then I’d like you to spank me, not too hard though.” You explain, biting your bottom lip as he nods in agreement. 

“We can do both those things.”

“But first I want you to lay down on the bed.” You clear your throat, not comfortable giving the instructions. This is his territory. 

He walks over to the bed, sitting down before laying back on the pillows. You crawl over him, straddling his legs, then moving until you’re sitting across his upper thighs, his erection standing tall against your stomach. 

“I want to touch you,” you admit, watching him blink in response. You reach up, placing your opens palms over his chest, feeling him twitch under your touch. Fanning outward you sweep your palms over his chest and toward his shoulders, sliding over warm skin. Both his hands are resting on your thighs. He sighs when you run your nails through the hair on his forearms and then lean forward to suck on the skin of his neck. 

A low groan leaves his throat as you nip at the juncture of his neck and shoulder and before you think better of it you place a kiss just under his ear. It’s a lingering touch and then you do it again and again moving downward until you find yourself under his jaw, scraping teeth over his five o’clock shadow. When you raise your head to look down at him, his eyes are closed, popping open seconds later. Staring at each other, his hands slide around to cup your ass cheeks, rocking upward as his cock rubs over your stomach. 

You shift forward and rub your clit against his cock, nose pressed into the side of his cheek. 

“Fuck my mouth,” you whisper.

Sam moves in record time, flipping you onto your back as you yelp in surprise. Getting off the bed he grabs you by the ankle rolling you onto your belly then turning you in a half circle until your head is hanging over the edge of the bed. 

“Open.” Your jaw falls slack as he slides the head of his dick past your lips and you suck hard, as he slides forward. “Take it,” Sam purrs, reaching down to stroke your cheek as his cock hits the back of your throat. You hum around his dick, let him push forward until his balls press into your chin. “Just like that.”

His deep voice conveying words of praise go straight to your clit, throbbing between your legs, triggering the slick that’s leaking from your sex. You let him fuck your throat looking up as he stares down at you with forced concentration. Without warning, he pulls out of your mouth leaving a trail of spit as he taps your shoulder like he’s tapping out of a fight. 

“Roll over,” he commands, big hands turning you over as you comply without hesitation. Head tilting backward over the edge of the bed, upside down. He places one hand at the side of your face, the other on his cock as he pushes back between your lips. “Open up.”

He slides his cock over your tongue and past your uvula as you swallow him whole. Pressing forward he watches the bulge in your throat, then reaches down to rub the outline of the head of his cock as you choke around him. “Fucking perfect.” 

He holds himself there for a five count, you know it well. He’s rough, but consistent which helps for things like this. The next one will be longer, but if you count to ten you know he’ll give you relief. 

He pulls out, drool leaking over the sides of your face as you gasp for air. Holding his spit-wet dick in his hand he rubs the head over your face, tapping your cheek several times before sliding back inside, right back into the deep stretch while you concentrate on breathing through your nose. 

This is one of your favorite things. While you knew you liked sucking dick, having him fuck your mouth as you lay on the bed is a whole other level. Your pussy is slick, throbbing with excitement as you gag around his thick shaft. 

“I can see my cock in your throat,” he observes, rubbing the bulge with two fingers. He pulls back, leaving you a mess of spit and tears, eyes watering, but you eagerly open back up, tongue out as he thrusts back in. “Do you like this? Choking on a cock?”

“ _Uhhh_ ,” you rattle, vibrating around him, unable to do little more than make desperate gurgling sounds. 

“I know you do.” He strokes your cheek, rocking forward, getting just a tiny bit deeper. “What do you say?”

“ _Huh ooo_ ,” is your version of _thank you_ as you swallow him whole. 

“Where do you want me to cum?” he grunts, pulling out. You look up at the sight of him holding his cock in his hand, inches from your face.  

“In my mouth,” you confirm, clamping your thighs together. “I want to taste you.”

“Open wide.” Reaching forward he gives your nipple a hard squeeze before jerks himself with the head of his cock on your tongue. A half dozen strokes later he's cumming warm and salty as you suck and swallow with fervor. “Keep sucking, just like that,” he instructs as your tongue gently swirls around the sensitive head. 

When he’s really into it he can stay hard after he cums. He’s done it plenty of times before. He can’t always get off again, but he can damn sure fuck you into next week. 

You carefully attend to his cock, rolling his balls in your hand until he’s sufficiently aroused and then he pulls you off his dick by your hair. 

“On your hand and knees,” he instructs, gesturing toward the bed. You scramble into position, feeling your pussy ache as he knees his way between your calves. “You want me to spank you?”

“Yes, please.” You look back at him, arching your back, widening your legs. 

“You’re going to get a spanking while my cock is in your pussy,” he huffs, running a hand over your lower back, down the crack of your ass. “Make sure you ask before you cum. No more rule breaking, not even on your birthday.” 

You swallowed his load before he told you to, part of you was wondering if he’d punish you for it. 

“I understand,” you confirm feeling the thick head of his cock sink into your slippery pink cunt. It’s an easy slide despite his size, but you're wet enough to take him to the root on the first stroke. He holds himself deep, balls pressed into your mound and then his hand comes down on your backside. 

_Crack. Crack. Crack._

It’s perfect. He knows your body to a tee, knows exactly how hard you like it. His harder spanks are saved for discipline and his softer ones are teasing, but this is the perfect sting. 

“It’s your birthday, twenty-nine would be the tradition, wouldn’t it?” He strokes in and out, nestling back inside before bestowing three more smacks on the other cheek. 

_Crack. Crack. Crack._

“Fuck,” you breath, clenching around his shaft. 

He pulls out, only to thrust back inside and then they come in rapid succession. Too many to count. All you can do is howl, twisting on his cock until he finally stops, both hands gripping your ass, squeezing. 

“Would you like to cum now?” His inquiry is accompanied by a series of shallow thrusts. 

“Yes.”

“How? Like this?” You’re not used to being asked for your preference and hesitate before answering. 

“Yes, but I want you to hold yourself deep and rub my clit.”

He snorts, leaning over your back. “Anything for the birthday girl.”

Pressing forward he stuffs your cunt until he’s right against your cervix, sending out those little sparks of pain you love so much. His middle finger finds its way to your clit, making soft circles and you’re already there. 

“May I cum?” you pant, eyes shut, mouth hanging open. 

“Yes.” 

It’s the only permission you need before falling over the edge and cumming around his cock. You jerk, moaning and whimpering as you tighten around his shaft. He takes his hand away from your bud but holds himself inside you until your orgasm begins to fade. He pulls out only to slide back inside again, thrusting slow and even, two hands gripping your hips. 

“We’re going to get one more out of you tonight.”

-

You’re sweating. 

You flex, blinking awake trying to figure out why you’re overheated only to find Sam wrapped around you, his chest pressed against your shoulder blades, soft belly at the small of your back. 

It’s not the first time. He often slings an arm over you in his sleep, but he’s never cocooned you before. You wiggle backward, testing the waters and his grip tightens as the arm over your side curls under your stomach, pulling you back into him. 

If he woke up like this you’re not sure what reaction he’d have. The two of you live in a strange world, a weekend relationship devoid of soft affection but always intense. The two of you have slipped into a safe space, an agreement and routine that seems to be working. This isn’t moving backward or forward, you’re stuck in a loop of sex and gratification that never fails to leave you somewhat crestfallen as you head into the week. You spend your time waiting until you’ll see him next, hoping for a little more. 

You lie there, half awake, body hyper aware of him holding you for nearly two hours. It’s morning when he finally rolls away, grunting in his sleep and flipping onto his stomach retreating back to his side of the bed. 

Sam’s sleeping belly down in the bed, mouth open as his back slowly rises and falls with his breath. You lay there, unmoving, watching his relaxed features, that handsome face looking almost boyish with his pink-flush cheek smashed into the pillow. He’d never let you gaze at him like this if he was awake, so you indulge while you can. 

There’s no need to look at the clock to know it’s early, the way the light filters through his windows shifts depending on the time of day. That and he’s not up yet. It must be before six if he’s still out like a light. 

The clock confirms it’s five forty-five and for once on a Saturday morning, you’re willingly awake before noon. He normally let’s you sleep in while he goes for a run and does a few hours of work. You give him one last look and gently crawl out of bed, pulling on white cotton panties and foregoing all other clothes, heading to the kitchen to make tea. 

You’ve just taken the kettle off the stove when you hear it, a shuffling behind you. It’s impossible to explain how you know it’s not Sam, but you do. You can sense it. Every hair on your body stands up on end and when you turn around you’re faced with a stranger standing in the middle of Sam’s kitchen. 

He’s tall, not as tall as Sam but a big guy and you’re instantly frozen in place, practically naked, blinking at the man in front of you. His shirt is spattered with blood, the red stains that are unmistakable. 

“Well shit,” he smirks, a grin tugging at his mouth as he eyes your naked tits. “He always had good taste.”

“Um,” you stammer, taking a step back. “Um, who-”

You can’t find the words, your brain shutting down as he gets closer. 

“Look at you,” he whistles, sauntering around you as you turn in a slow circle to keep him in your line of sight. His eyes dropping down the length of your body, head to toe. “How much does a guy like Sam pay for a girl like you? Do you charge by the hour or the night? I mean, I’ve been to Vegas, fucked my fair share of working girls but hot damn sweetheart, you are something special.” 

It’s at that moment that your thoughts come together to form a coherent thought. This is Dean, Sam’s brother. 

“ _Pleasedon’thurtme_ ,” you squeak out in one quick utterance. 

“Don’t worry sweetheart. My brother has never been very good at sharing anyway.” His eyes hone in on the fresh bruises on your hips, leftover handprints.  

“Wh-what do you want?” you stutter, now shaking in fear. Dean closes in and you back up into the counter, trapped by his advance. 

“Don’t worry,” he eyes your tits again. “Nothing you can give me, at least not right now.”

“Get away from her.” Sam’s voice booms from across the kitchen, standing bare-chested in a pair of pajama pants, eyes on fire. He looks from Dean to you, extending a hand. “Come here.” 

“We were just getting to know each other.” Dean offers a lopsided grin. 

Eyes glued on Dean, you inch sideways until you can scurry across the kitchen, letting Sam pull you to him. 

“Sam,” you look at him, eyes wide. 

“It’s okay.” He takes a half step in front of you, putting himself between you and his brother. “What are you doing here, Dean?”

“Did I come at a bad time? I understand if you wanna be sure you get your money’s worth before we get down to business.” 

“She’s not a hooker,” Sam clarifies, tilting his head, eyes never leaving his brother. 

“Yeah,” Dean smiles, making a production of leaning to the side to look at you. “Didn’t think so. Good for you, getting back on the horse after all these years. I’m happy for ya.”

“Cut the shit,” Sam steps forward and you move with him, pressing against his back. “What the hell are you doing in my house? Are you trying to get me arrested?”

“Trust me.” Biting his lip, Dean chuckles to himself. “This is the last fucking place I want to be. But I need you, Sammy, there’s some bad shit about to go down. End of the world type stuff. Dad and I need you.” 

“You’ve gotta be kidding me.” Sam snorts, his posture softening. “No.”

“Tell you what. How ‘bout you put your girl back to bed and we talk about this alone?”

“How about you get the hell out of my house?” Sam counters. “You must be high if you think I would ever do anything for you or dad.”

“Just hear me out, Sam.” All the playfulness drains from Dean’s face. “Dad went on an a...hunting trip. He hasn’t been home in a while.” 

“How is this any different from any other time?” Sam shakes his head. “You know this feels familiar. It’s been fourteen years since the last time you showed up with this same story. I went with you and Jess ended up dead. You ruined my life and Dad showed up when he damn well felt like it. So no, there is no way in hell I’m going anywhere with you.”

“We need you.” Dean’s mouth pulls tight. “I know you’ve got a whole white collar thing going on and a life, a girlfriend. I wouldn’t ask if I had a choice.”

“There’s always a choice Dean. I made mine a long time ago. Dad said if I left not to come back and I haven’t. So get the fuck out of my kitchen.”

“Sam,” Dean takes a step forward. “This is your family.”

“No,” Sam spits back. “Family was an illusion. A convenient guilt trip to get me to do what you and dad wanted. I don’t have time for _family_ , Dean. My life is full up.”

“Okay,” Dean looks at the floor, before leaning to the side to look at you again. “Nice to meet you-”

“Stop talking to her.” Sam’s voice is colder than you’ve ever heard him, venom simmering under his words. “You stay away from me and you stay away from her. You hear me, Dean?”

“I hear you.” Dean waits for a beat, looking from Sam to you and then he’s gone just as quick as he came. 

“Sam,” you sputter as he turns to you, placing a hand on each shoulder. 

“We need to talk.” 


	13. Thirteen

_Dean._ The look in his eyes will forever be seared into your brain. 

“We should call the police,” you panic, starting toward the bedroom for your cell phone. 

“Y/N, stop.” Sam catches you by the arm. “No police.”

“But Sam!” You look around wildly, half expecting Dean to pop back around the corner. “What if he comes back? We have to tell someone-”

“No,” he barks, sitting you on a stool at the counter. 

He disappears for a moment, returning with one of his sweatshirts and hands it to you, silent as you pull it over your head. 

“I need you to make a promise to me, here and now, that you will never tell anyone Dean was here.” His face is gravely serious, standing in front of you like a father scolding a child. 

“But-”

“No caveats. This is non-negotiable. You will never tell another living soul about this. Understood?” 

“I-” you sputter, trying to make sense of this. Why would he ever want to protect a person that’s done such heinous things? In the end it’s the submissive part of you that answers on autopilot. “I understand.”

“Jesus Christ!” Sam explodes with anger, his fist connecting with the door of the refrigerator. He punches it three times in rapid succession, clutching bloody knuckles looking in horror between him and the dents in the stainless steel. “I can’t fucking believe he showed up.” 

“You hurt yourself.” You start to get up but he takes a step back, lip curling as he glares at you. 

“Stay where you are.” He’s vibrating with anger, this is a side of him you haven’t witnessed before. He’s normally controlled to a fault, but there’s no containing this outburst.  

You draw in a breath, sitting back on the stool, watching him seethe. He yanks open a drawer and wraps a hand towel around his knuckles. 

“If you ever see Dean again, if he tries to contact you, you come directly to me. Tell me immediately.”

“What does he want with me?” There’s fear rising in your chest. You’ve read about the things that he’s done, sick, twisted acts, some of which are utterly unspeakable. “You’re scaring me.”

Your voice cracks and it seems to jog him out his blistering fury and his face goes even, that self control slipping back into place. 

“There’s no reason to be scared. He won’t hurt you, but if Dean came here after all this time it means he’s serious. He’ll come back. If I were him, I’d use you to get to me. The Winchesters are persistent above all else.” 

“How can you say he won’t hurt me?” You’re still in shock, searching his face for some kind of understanding. “After all the things he’s done...”

“I’m going to have to ask you to take a giant leap of faith and just trust me when I say that there are things about Dean, about my family and my past, that aren’t what they appear to be. Dean is a son of a bitch but he hasn’t done half the things they say he has.”

“How do you know? How can you be sure?” 

“I just do. I know my brother, he’s changed but not that much.”

You gulp, trying to wrap your head around all this information. There’s a wet sensation on your knee and you look down to find a drop of blood, dripping from the soaked cloth around his fist. 

“You should go to the hospital, you might have broken something.”

“I’ll survive.” He winces, taking off the rag to inspect his bloody knuckles. 

“I’ll do what you asked, but I don’t understand,” you insist. “I need you to explain to me how it’s possible he’s on the FBI’s most wanted list and you’re saying he’s basically harmless.”

“I’m not saying Dean’s harmless, he’s far from it. He’s lethal, it’s the way my dad raised us. But he’s more of a... _vigilante_ than a killer. He and my dad are into some dark stuff, occult bullshit. I separated myself from that world a long time ago. It’s just a bunch of wack-a-doo superstition. ” 

“You’re _sure_ he won’t hurt me?” you press, coming down from the adrenaline of the situation. 

“If I thought you were in harm’s way I’d call the police now and have him arrested. If I thought he’d hurt anyone who didn’t deserve it, I’d turn him in.” He looks at you, mouth tight. Whatever he’s thinking about he doesn’t let on as he stares to you. He grunts, eyes fluttering closed as he flexes his wrist. “I am going to need to see a doctor.”

“Do you want me to drive you?”

“No. That’s why I have a driver.” He shakes his head. “You may stay here or go home, whatever makes you feel safer while I’m gone.” 

“Would you prefer if I left? I mean after everything-” 

“I would _prefer_ that life moves on despite my brother. I expect you to be here tonight. I have plans for you, and you don’t want to disappoint me do you?”

His eyes narrow, looking at your bare legs and you almost forget how to breathe. 

“Never,” you confirm. “Never.” 

-

As the days pass the looming threat of all things Dean fades. For the first couple of days you were sure he was going to appear around every corner, but life goes on and the _most wanted_ Winchester is nowhere to be found. But he’s always in the back of your mind, the way he looked at you, the coldness in his eyes. In Sam’s own words his brother _is lethal,_ a description that’s less than comforting. 

But the fact is you trust Sam. You trust him with sex and you trust that when he tells you that you’re safe, you are in fact, just that. 

 

**Three Weeks Later**

Sam has been in Japan for almost two weeks but it feels more like two years. You’d fallen into a comfortable routine and it’s strange to go more than a week without being in the same room with him. 

Your phone vibrates at eleven o’clock sharp, signaling Sam’s incoming video call. You swipe to answer, glancing up to ensure the living room curtains are shut. The last thing you need is one of your neighbors watching you masturbate on command. 

“Hi,” you smile as his pixelated face appears on the screen. 

“Hello,” he replies, distracted by whatever he’s looking at. His face becomes clear as the connection strengthens. This is his lunch break which inevitably means time will be limited. His eyes snap between something he’s reading and your image on the screen. “Set your phone up so I can see your entire body.”

“Okay,” you respond, getting up to prop your phone on a stack of books in the middle of the coffee table. This is not the first night you’ve been in this position and you’ve perfected the setup. You take a seat on the couch, making sure you’re in the frame as he glances up. 

“Take your clothes off. Everything.” He forgoes whatever else has his interest, focusing solely on you, watching stoically as you strip down, shimmying out of your panties then letting your bra fall to the floor. 

There’s a faint knock coming from his end and he instantly looks annoyed, looking up as he calls to whoever it is. “Come in.”

“ _I don’t want to bother you during lunch Mr. Winchester_ ,” Lexi’s voice is immediately recognizable in the background. You lean closer to the phone, listening carefully. “ _I just wanted to pop in and make sure you have everything you need_.”

You know that tone, playfully and airy. It’s the same one she uses at the bar when she’s trying to hook up with some junior associate. She’s flirting with Sam Winchester. You assumed that no one would have the balls to approach him but you’ve clearly underestimated her. 

“I do,” Sam stares at her with his trademark uncomfortable, unwavering stare you’ve been on the receiving end of from time to time. “Have everything I need.”

There’s silence. She’s obviously still there because he hasn’t turned his attention back you. 

“You can go.” He watches off the screen and you wait until you hear the faint click of a door and he turns back to his phone. 

“What is she doing-” you start but Sam is already moving on. 

“She isn’t your concern.” He chastises you immediately, bringing on all the familiar feelings of subjugation that never fail to turn you on despite your own shame. “Open your legs and touch yourself. Make sure I can see your cunt.” 

You lean back on the couch spreading your legs wide. One finger slides into your mouth, parting your lips just enough to flick your tongue against it. Then you run your fingertips lightly down your body, over your breasts. 

Sam shifts, clearing his throat as he settles in to watch you. You wonder if he’s touching himself, stroking his own cock or is he just directing and watching? One never knows with him. 

“Are you wet?” he asks firmly. 

You continue to move your hand down across your belly, over your mound and slipping one finger between your folds, breath catching in your throat. 

“Yes,” you nod, feeling your own slick. 

“Did you masturbate this morning like I told you to?” he inquires like a teacher ready to reprimand a petulant child. 

“Yes,” you confirm with a whimper, slowly dipping a finger between warm flesh. 

“Good. We’re going to try something different. Get the oil out of the box and oil yourself up.”

Sam presented you with a box of special toys before he left on his business trip and the two of you have been working your way through all the contents. 

You find the bottle of massage oil and pour it into your hands, rubbing it over your arms and neck, then running your hands down the sides of your breasts. You lift one leg onto the coffee table giving the camera a better view of your pussy and you work on one leg. Then repeat the process, stroking and caressing your inner thighs. When you are done you sit back, presenting your now glistening body for his inspection.  

“Very nice,” his eyes fall from your tits to your pussy, tongue darting out. “Grab your breasts.”

You slide both hands over your breasts, feeling your nipples harden with a soft moan of anticipation. 

“Not that like,” he snaps, shaking his head and your eyes shoot up, hands falling to your sides. If there’s one thing you truly hate, it’s his disappointment. It’s not often that he corrects you so severely but being relegated to only video chat has been testing his patience. “Listen to me. From now on your hands are my hands. When I tell you to touch yourself, I want you to picture my hands doing the touching, do you understand?”

“Yes,” you nod, sitting still, legs spread. 

“Put more oil in your hands,” he instructs, leaning closer to his screen. 

You comply, picking up the oil and spreading it over your palms. 

“Now,” his head tilts, jaw tightening. “Pinch your nipples _hard_. Your hands are my hands and tonight I’m going to be rough. You know the way I touch you. Do it.”

You squeeze your nipples, twisting them harder than you intend to. A cry escapes your lips as you feel yourself sliding into that place where you turn yourself over to him. Your hands continue to pinch harder and harder, biting down on your nipple the way he would until you cry out again. 

“Harder” he encourages. 

You pull, feeling the stretch and gripping as hard as you can, gasping in pain that shoots from your tits to your pussy and becomes instant arousal, your clit aching between your thighs. 

“Good girl. Spread your legs wider, keep pulling on your nipples with one hand. With the other, shove your fingers into your cunt.” 

Hooking one leg over the arm of the couch you lean back, offering him an unobstructed view. Giving your breast a sharp tug you slide a hand between your thighs, two fingers sliding into your slick, deep and fast just like when he fingers you. It feels almost as if he is the one touching you as you fuck yourself rough and quick. The familiar wet sound of your pussy taking your fingers fills the room as you close your eyes and lay your head back, the world shrinking away while you imagine Sam touching you, tugging and pulling, fucking you hard and deep. A series of short, sharp cries leave your mouth as the hot flush of an orgasm begins to build. 

“Can I cum?” you ask, already knowing the answer. 

“Absolutely not,” he quips. 

Mustering every last ounce of self-control you pull your hand away, whimpering when your fingers leave your body. You’re quivering, shaking with need. It’s been nine days since he let you cum and you’re practically vibrating with need. To be fair he gave you a warning. No orgasm’s until he returns from Japan, you’re not allowed to cum without his fingers or his cock in you, no exceptions.  

“We’re going to try again. Spread your pussy open and pour the oil over your cunt.” 

Your fingers slide back between your legs, spreading your lips open. You pick up the oil and pour it slowly in a thin stream over your folds. The sensation of the cool oil dripping over your exposed clit and between your legs makes you shiver. 

“This time fuck yourself with three fingers.”

Running your fingers over your sex, the other hand finds your breast again, clamping down painfully hard on one nipple as you slide three fingers inside your cunt. You gasp, rocking your hips against your hand, driving deeper just like he does. 

“Spread your pussy open and angle your hips toward the camera. Let me see you.”

You inch forward, pushing your fingers deeper still and scissoring them open, forcing yourself open for his viewing pleasure. There’s an incredible feeling of vulnerability, exposed and humiliated as you hold yourself open for him to watch you. 

“Your pussy is begging for it, but I think you’re missing something else. Get the vibrator out of the bag and then lube it up. Make sure you cover the whole thing.”

“You want me to…” you trail off, sitting up to stare at him. He’s close to his phone, his face is the only thing visible. 

“You know exactly what I want you to do.” 

He’s been fixated on one specific torment this entire trip. 

Your hands are nearly shaking as you reach for the box, withdrawing a rather powerful vibrator roughly twice the width of his thumb. You lube up the wand squeezing a thick ribbon of jelly along the hard plastic, all the while feeling the oil already slick between your thighs. 

“You know what to do.” He cocks an eyebrow as if he’s expecting you to protest. 

Feeling the heat in your cheeks you spread your legs again, pressing the blunt end of the vibrator against the tight ring of muscle between your butt cheeks. There is nothing that brings more shame or more arousal than this. 

“Good girl. All at once. You’re going to tell me how much you want it up your ass when you push it in.” 

You shudder in complete embarrassment. He knows exactly what this does to you. It’s degrading and exhilarating all at the same time. You’re ashamed to admit that you enjoy it.  “But-”

“Do it. Say it loud. Push it in. Right now,” he grits out. 

You take a deep breath, then in one smooth motion slide the vibrator into your ass as far you can. “I want it so bad, so deep like this... _oh fuck_.”

Before you have a chance to adjust he continues. “Turn it on.”

“I can’t,” you whimper, squirming as you hold your legs open. 

“Why?” He tilts his head, eyes narrowing at your refusal. 

“I’ll cum,” you admit. 

“Turn it on. And don’t you dare cum without permission. If I have to tell you again you’re not going like what happens when I see you in person.”

The vibrator is one of your favorite toys, but it’s a source of torment as well. He knows full well it makes it nearly impossible to not cum and he’s become fond of using it on you, refusing to allow you to orgasm while making you masturbate with it both anally and vaginally. 

Reaching between your legs you turn the small knob at the base and it comes to life, sending shock waves of pleasure through your body. 

“Oh, oh, oh,” you pant, eyes closing as you writhe and wiggle. 

“Does it feel good?” He loves to make you admit how much you enjoy these depraved acts. 

“Yes,” you moan, hands rubbing down the tops of your thighs, trying to hold on to what little control you have left. Your orgasm is building, it wouldn't take much and if he makes you touch yourself again there will be no holding back. 

But instead, he does something equally cruel. 

“I think that’s enough for now,” he explains flippantly as if he’s already moved on to something else. “Turn it off and clean yourself up. I’ll see you tomorrow, same time.” 

The screen goes blank when he hangs up leaving you on the edge of pleasure and desperation.

-

Three days later you’re locked in a windowless conference room, waiting for Sam’s call. He’s an hour late, which is unheard of. It’s 11 am your time which means it’s midnight there.

Staring at the screen you watch the minutes tick by, trying to make a decision. What if he forgot? That’s unlikely. Sam doesn't forget anything. Maybe he fell asleep? 

He’s flying home tomorrow, it’s possible he just lost track of time in preparation. Your thumb hovers over the call button, tapping it as Keith’s name appears on the screen. 

After exactly three rings the line picks up, the screen fumbles for a second and Lexi’s face appears. She looks just as surprised to see you as you are her. Your mind races, it’s late and she has his phone. 

Pepper doesn’t even touch his phone. 

“Hey, umm,” you stumble trying to think of a cover. “Did I dial the wrong number?”

“No!” She smiles wide. “That’s so weird, your name came up as Hester something or other. His phone must be messed up.”

You nearly choke, realizing Sam’s reference to the Scarlet Letter and thankful that Lexi isn’t more well read. 

“Yeah, that’s so weird. Why do you have his phone? It’s super late there isn’t it?”

“You wouldn’t believe me if I told you,” she chatters on. “I was... _oh, you have a call_ ,” she looks off-screen. “ _I answered it for you I hope you don’t-_ ’

Sam’s face is immediately on camera, looking at you like he’s ready to murder someone. “I’ll see you when I’m back in the office.” 

 

**Two Days Later**

“Hi,” Lexi drapes herself over cubicle wall of your desk. “I am _so_ glad to be home.”

You haven’t spoken to Sam since that night when she answered his phone. While you understand he doesn’t always have time to give you his full attention you’re still uncomfortable with the circumstances and eager to see him again. Lexi is the last thing you need right now. 

“Well,” you swallow your feelings, it’s not her fault after all. She doesn’t know she’s encroaching into your territory. “Welcome home. You didn’t like Tokyo?”

“Oh you know. Pepper is a bitch even when she thinks she’s being nice and the food was disgusting…” Her finger trails along the edge of your desk, biting her lip as she looks up at you, almost vibrating with whatever she wants to tell you. “But _other things_ weren’t so bad.”

“Oh?” You turn back to your screen, unable to look at her. 

“You’re going to think I’m crazy and you have to promise me that you’re not going to tell anyone.” 

“Maybe you shouldn’t tell me then? If it’s supposed to be a secret.”

“You’re no fun….I have to tell _someone_ ,” she whines, pulling a chair over and inching right up into your personal space. “This is so wild, but Sam and I got sort of... _close_ during the trip.”

Every inch of your body goes hot, instant adrenaline pumping in your veins. 

“What exactly do you mean by _close_?” you inquire, folding your hands together in your lap. 

“You know how it goes, one thing leads to another. Late nights in hotel rooms, he practically asked me to stay the night with him. I know everyone thinks he’s a hardass but under all that he’s just a man. He’s kind of handsome, don’t you think?” 

“I haven’t given it much thought.” You clear your throat. “Sorry, I have to pee.”

Before Lexi has the chance to say another word you’re up and out of your seat, locking yourself in the nearest bathroom feeling a combination of anger and nausea. 

You’re shocked by your own reaction. If you’re honest with yourself there have been certain feelings creeping in, it’s unavoidable when you spend as much time with someone as you have with Sam. You tell yourself you’d feel the same way if he was just a friend. He’s always been crystal clear about what you are to him, and you’ve used that division to keep a deeper attachment from forming, or so you thought. But the idea of Sam and _Lexi_ of all people is bringing emotions to the surface you’re not at all ready to deal with. 

You know she was in his room. She answered his phone, looking less than professional and he chose not to offer any explanation. Is it possible? Would he fuck her? Why not? You have no power to enforce your contract, it’s for _his_ safety, not yours. Being reminded that you were forced to sign a piece of paper, to agree to his terms brings your anger and frustration to a head. 

And the things he’s had you do while he’s been gone, you’ve acted like a whore performing for him, complying with every request with enthusiasm, only to have Lexi talk about how close they’ve gotten. 

Wiping a tear from your eye, you pull out your phone.

_**Y/N:** _ _I need to talk to you._

You send off the message instantly filled with regret. You’re upset, you should wait until you’ve got your emotions under control. Taking a series of deep breaths you look at yourself in the mirror, staring at rosy cheeks and wild eyes. 

You phone dings twice.

_**Keith Campbell:** _ _I’m busy today._

_**Keith Campbell:** _ _Is it important?_

You stare down at the phone, mouth twisting as you debate your response. 

_**Y/N:** _ _Yes._

There’s almost no delay before his answer pops up. 

_**Keith Campbell:** _ _Come to my office now._

After smoothing back your hair you take a final breath and head toward the elevators. Pepper doesn’t even look up as you pass her desk. Instead, she mumbles something about Sam warning her you were headed up and waves you inside. 

Sam’s at his desk, focused on his laptop. He glances up for split second, looking rather unhappy with your interruption. “Make it quick.” 

“Don’t talk to me like that,” you snap, surprising yourself as much as him. His eyebrows shoot up, all attention focusing on you as he stands up slowly, clearly not in the mood for a challenge. 

“Excuse me?” He walks around his desk, mouth twisting in displeasure. 

“Did you fuck Lexi?” You just put it out there. On the way up to his office you went over and over it in your brain, you had a whole speech prepared about expectations and trust but now as you stand in front of him it just tumbles right out. 

For a split second he looks genuinely perplexed, then his grave expression turns into amusement as he crosses his arms over his chest, examining you. 

“Why are you asking?” His question is calm but leaves no room for debate. 

“Because she was in your room, she answered your phone...and she just told me…” As you say the words you’re already realizing you don’t really believe it yourself. Sam and Lexi; it’s ridiculous. Closing your eyes you shake your head in embarrassment. “I’m overreacting, aren’t I? Lexi exaggerates everything.” 

“Yes, she does.” Sam nods, his eyes falling down your body. It’s been fifteen days since you’ve been in the same room and there’s no doubt he feels the same arousal at your physical proximity. “That not to say that she didn’t try. Your friend put me in a series of incredibly inappropriate situations that I don’t wish to relive, especially with you. She won’t be working for me again.”

“Good.” You look at the floor, pressing your lips together. “To be clear, Lexi isn’t my friend.”

“I don’t care about semantics.” He sighs, pinching the bridge of his nose as if this conversation is really taking a toll on him. “Now, if you don’t have any other burning questions, _you_ need to leave because _I_ need to focus. I have a week’s worth of reports to review and you are the ultimate distraction.”

“Oh, o-okay,” you sputter, both offended and flattered. “Sorry for bothering you, I was just, I...I’ve just got a lot of pent up frustration and then she said what she said and I…”

“Got jealous?” One eyebrow shoots up and you’d swear there’s a pull at the corner of his mouth. A ghost of a smirk. 

“A little,” you confess.

“Go,” he waves a hand, walking back around his desk. “Come over tonight. I’ll send a car for you around nine and we’ll take care of your frustrations.”

“But it’s Thursday?” You hesitate, unprepared for the last minute surprise. 

“I’m aware,” he stares you at again. “I’ll see you tonight.” 


	14. Fourteen

The drive from your apartment to Sam’s house takes nearly an hour. The city fades into suburbs and then becomes even more rural as you escape the city. You know this route well, traveling it at least twice a week for the last several months. His modern mansion is tucked away on a sizable piece of land assuring him the privacy he craves. You can’t help but wonder what the night will hold. Your stomach is uneasy, a combination of nerves and excitement that’s all too familiar when it comes to Sam Winchester.

You can’t believe that you actually did it, you went to his office and confronted him about Lexi. It was an idiotic move. As much as you hate to admit it, you care what he thinks of you, a great deal actually. And now you’ve made yourself look like a jealous girlfriend. You can only imagine what he must think. It’s a coin toss how he’ll react once you’re in the privacy of his home. He may reprimand you or perhaps he’s been craving you just as much as you have him. After weeks away you’re hoping for some well deserved relief.

At least your unscheduled visit to his office garnered you an invitation for a Thursday night encounter. Weeknights have always been off limits, but he seemed more than willing to make an exception.

You let yourself in the front door, sliding off your shoes and padding down the hall to the living room where you find Sam sitting in an armchair, reading a book. The sun has already set and the only lights in the room are that of a dim reading lamp and the flame glowing in the electric fireplace.

“Take your clothes off,” he commands without looking up.

You watch a moment as he turns the page, fixated on his book as you begin to undress. You’re well aware there must be something wrong with you because his utter disinterest is sometimes what flips a switch inside you, turns on your need to please him.  Slipping off your dress, you unhook your bra letting it tumble to the ground, leaving you nude in the flickering firelight. Your hair is still up in today’s bun and you unpin it, letting it fall around your shoulders.

He’s moved the coffee table out of the center of the room and there’s a square black box on the floor in its place.

You wait, shifting your weight as your nipples go rock hard, cold shivers traveling from head to toe.

Sam carefully bookmarks the page and sets the book on the table beside him. Then he takes off his glasses, setting them atop the book. He examines you, head tilting as both his arms extend along the armrests of the chair.

“Seeing you in the flesh is much more satisfying than over video,” he comments, even and measured. “Tell me, do you enjoy the things I have you do to yourself?”

You swallow, the ever present blush creeping into your cheeks.

“Yes,” you whisper, eyes locked on his.

“What about it do you enjoy most?” His thumb rubs against his middle finger, a telltale sign that he’s already thinking of new ways to torture you.

“I-” You stop to think about the last few weeks and his box of toys that had you completely and utterly embarrassed and on the edge of pleasure every night. “It makes me feel like a whore, to do those things to myself. I think it’s the idea of you making me do them that gets me off.”

“You could say  _no_ ,” he offers casually.

“I suppose, but I like to pretend that’s not an option,” you admit bashfully, hands clenching and unclenching at your sides. Your clit is already throbbing, the conversation alone sending little waves of pleasure between your legs.

“You like to feel controlled?” he clarifies, tongue darting out to lick his lips.

“By you, yes. I love it.” Your confession is not anything you’ve ever said out loud before but it’s unabashedly true. The idea of giving yourself to him for his own pleasure is what most excites you.

“Do you like to be called names? Whore? Slut?” Despite everything you’ve done up until this point he’s never directly called you names. He’s told you to suck his cock like a whore and to fuck him like a slut, but never outright used them.

“Not all the time. But sometimes I think I would like it.” You’re honest because Sam can handle the complexity of your desires. He himself has many layers and understands not everything is black and white, yes and no. “It turns me on the most when you make me say those things.”

“Would you like that tonight?”

“Yes,” you nod, squeezing your thighs together.

“Good. Thank you for your honesty,” he nods, taking a breath, glancing at the mound of your pussy. “Next we need to talk about your punishment.”

“Punishment?” you question surprised.

“Yes. I’ve been unhappy with you twice and we need to talk about both times. First, you came into my office today and questioned me about Lexi. I told you when this arrangement first started that you would be my only sexual partner. That was part of our agreement. Do you remember?”

“Yes,” you nod, looking at the floor. You want to remind him that he also jumped to conclusions about Max, but this isn’t the time or the place. And to be honest, punishments are often one of your favorite activities. “I’m true to my word. Do you understand?”

“I understand. I’m sorry.” You shake your head, doing your damnedest to look apologetic.

“I hate it when you say that. Don’t be sorry, change your behavior. Which brings us to the second issue. When I tell you to do something, you do it. If I tell you to turn a vibrator on, you turn it on. I don’t like having to tell you twice.”

Something about the combination of his tone and the words makes your legs weak. You’re not sure what’s wrong with you for liking this and you’re probably going to hell for getting off on it, but  _fuck_  if he doesn’t make your pussy ache.

“It won’t happen again.” You look up, meeting his unflinching stare.

“I was going to come home and fuck you but I’ve decided that you need a reminder about who’s in charge,” he snaps, jaw ticking.  “Ask me for it.”

“Please show me you’re in charge,” you respond without hesitation. “I need to be reminded.”

“Yes, you do,” he sighs, sitting up. “Open the box.” He gestures to the shiny black box on the floor. You kneel down, taking off the lid to find a series of sex toys. There’s a thick black dildo, several butt plugs in various sizes, a small vibrator, a ball gag, and a ring gag. “We’re only going to use one of these tonight, we’ll save the rest. Take out the largest plug.”

You look up at him, then down into the box picking up the thick, cold metal plug, feeling the weight of it in your hand.

“Now, turn around, get down on your hands and knees. Spread your legs wide so I can see your cunt and your ass.”

There’s that conflicted feeling, the one that all your encounters start with. You turn around, getting into position and presenting your backside to him, knees grinding into the carpet.

“I would say you could use lube, but it doesn’t look like you need it you’re so wet. Stick it in your pussy, get it wet enough to slide up that tight little ass.”

You whimper, a shaky sound erupting from your throat as you reach between your legs and ease the metal into the slick between your folds. You rub the tip over your clit, bringing a jolt of pleasure before pushing it into your dripping sex.

On hands and knees in his living room is about as submissive as things have gotten up until this point but you’re not surprised at the way your body is reacting. This is a vulnerable and shameful position, but also thrilling.

You make slow circles feeling the plug in your pussy before pulling it out. Suddenly his hands are on you, one hand on your hip, the other coming down on your ass cheek with a resounding  _crack._

“Fuck!” you wheeze, rocking forward.

He takes the plug from you, pushing it back into your cunt until it’s all the way inside, the base between your lips. He leaves it in place for a moment, rubbing your clit with his thumb as you pant, pushing back into him. Before there’s too much pleasure he pulls it out with a wet sucking sound.

“Now,” his fingers are spreading your cheeks wide and the cold wet tip of the plug meets your puckered hole. “I’m going to push this in. While I’m getting it into place I want you to tell me what a whore you are and how much you want it. Do you understand?”

“Yes,” you gasp, nodding enthusiastically as he begins to push hard. You can feel your body stretching open, the pain and the burn that morphs into liquid heat between your legs. “I’m a whore. I want it deep, please. Oh god, please harder.”

With a final push, the plug sinks in, popping past the ring of muscle. You groan, dropping your chest down onto the carpet as he gives your ass a couple of hard swats.

“Come,” he instructs, sitting back in the chair, spreading his legs. “Kneel here.”

You shuffle over to him, feeling the plug shift inside you, a delicious stretch that makes your empty pussy clench around nothing.

“Now, I think it’s time for something new.” He looks down at you with a dark affection, his hand cupping your jaw, thumb sliding along your lower lip. “We’re going to add a little incentive for you going forward. This weekend you’re only allowed to have an orgasm if you have my cum in your mouth. Which means if you want to cum tonight, you better start sucking.”

You stare at him, genuinely surprised, your cunt and ass tightening around the plug in arousal. Without saying a word you reach out, unbuckling his belt, easing his throbbing erection out of his trousers. He’s clearly been hard for a while, the head of his cock is almost purple and leaking pre-cum as you lean forward and seal your lips around the head.

For the first few minutes, you suck on just the tip. There are times when he insists that you deep throat him right from the get-go, but you prefer this, suckling on him like you’re starving for it as your tongue slides against the little v under the head of his cock. It’s been weeks since you’ve had him in your mouth. This is something you really do love.

With a moan and a breath, you take him deep, your pussy twitching in delight as you taste the pre-cum on your tongue and then he slides down your throat. You moan again vibrating around his shaft and he groans, taking two big handfuls of your hair.

“Fuck,” he murmurs, more breathless than usual.

Bobbing up and down you keep him stuffed down your throat, breathing carefully through your nose, even and measured. It’s a skill you’ve honed over time, and now that you’ve perfected the technique and know how to fully relax your throat, you can stay like this for longer and longer stretches of time.

He tugs hard, hair yanking at your scalp and you come off him with a pop, drool dripping down your chin as you look up, waiting for further instruction. You hand is resting on his thigh and he takes it, guiding you to cup his sack.

“Do you feel how heavy my balls are?” His mouth falls open as you gently roll his package in your hand. “I haven’t jerked off in two weeks. I’ve been saving all this cum for your hot little mouth.”

“ _Oh god_ ,” you blurt out, the words tumbling out in a whimpering sigh of lust and excitement. Your pussy throbs and you swear you can feel your heartbeat in your nipples now.

“Suck on them,” he instructs.

Leaning forward you let the weight of his spit-wet cock rest on your face as you open your mouth and carefully suck one of his testicles inside. You’re gentle but consistent, rolling him over your tongue as his cock rubs over your nose and forehead. You move to the other side, tonguing him with care until he pulls you back up, ready for you to attend to his dick again.

You engulf his cock with unbridled enthusiasm, making small eager noises as you work the entire length of his shaft.

“Ask me for it,” he grits out, fingers digging into your scalp.

You look up, popping off his cock, wiping your chin with the back of your hand.

“Please cum in my mouth,” you implore, squeezing your thighs together you look up at him, eyes blown wide with lust, one hand wrapped around his length. “I want it so bad,  _please_  cum in my mouth.”

“Such a good girl,” he praises, wrapping his giant hand around your head, angling his cock back into your mouth. “Suck. Don’t stop until you have a mouth full.”

Diving right back in, you suck and lick, desperate for his orgasm. This submissive side of you gets almost as much pleasure from him cumming as you do from your own orgasm.

When he gets close he grunts twice, his hips bucking up and tapping the back of your throat, then he finishes. He spurts thick ropes, warm and thick over your tongue as you resist the urge to swallow, keeping all of his seed in your mouth as instructed.

After several heavy breaths, he pulls your mouth off him, grunting in satisfaction as you sit back on your heels.

“What do you say?” he asks, stroking his own cock base to tip.

“ _Hank ooo_ ,” you garble, waiting for his next command.

“Get up here and sit on my cock.” He grabs a fist full of hair, pulling you up into his lap. There are times when he can stay hard after cumming the first time but there’s no real guarantee and that’s what he’s betting on. You’re going to work fast and hard for it if you want to ensure your orgasm.

Straddling his hips you sink down on his erection, letting him sliding into your desperate, drooling pussy.

“Let me see.” He pats your jaw. You open wide, sticking out your tongue, showing him your mouth full of creamy white. “Good girl. Now, use my cock to make yourself cum.”

You don’t need to be told twice. You begin sliding up and down his dick, letting your clit meet the base of his cock with each pass. The stretch is wonderful, between the thickness of the shaft and the plug nestled deep in your backside, it’s almost as challenging as the first time.

Sam takes your wrists, twisting both arms behind your back and pinning them together at the base of your spine. You have to concentrate, keeping your thighs and hips in balance and you ride him.

The taste of him is salty and familiar on your tongue, this new requirement only adds to the building of your own peak.

Keeping your hands in place with one hand, the other hand moves to your breast, squeezing the nipple and twisting hard. You’re there, right on the edge, everything between your legs slick and begging for release.

“ _An I um?_ ” you struggle to ask for permission.

“Yes,” he twists your nipple just a little further as your orgasm sweeps through your body from head to toe. Just as the satisfaction begins to fan out he gives his final order, “swallow.”

You immediately swallow his load, gasping as your pussy pulses around his cock and your ass grips the plug. You tug at your arms out of instinct but he holds firm while you shudder and shake, cumming hard with him inside you.  

“Holy shit.” You quake, going slack, then slumping forward into him. He releases your wrists, both his hands cupping your ass as you lay your head on his shoulder. “Thank you.”

“You’re welcome,” he sighs, squeezing your ass, seemingly enjoying this part as much as you are.

-

“Tomorrow you’re coming with me to an…exclusive gathering.” He leans out of the closet, unbuttoning his dress shirt with two hands.

“That sounds ominous.” You sit back against the pillow.

“I’m assuming you’ve heard of Nick Luster?” he queries walking from the closet to the bathroom.

“Are you kidding me?” You’re suddenly uneasy. Nick Luster is a billionaire who’s made a name for himself by gaining a reputation as an eccentric recluse. “I don’t think there’s anyone who hasn’t heard of him.”

“He’s having a what he calls a ‘dinner party’ and you’ll accompany me.”

You’re taken aback by the statement, but wary for what it means. “I have two questions.”

“What?” He sits on the edge of the bed, tugging his socks off one at a time.

“First, I thought us going to some high profile place together was a huge no-no. And isn’t he a total Howard Hughes type? I’ve heard he hates people and now he’s having a dinner party?”

“There couldn’t be anything lower profile than an event at his home. He’s nothing if not thorough, the guest list is vetted. Every person is scanned for electronic devices, you’ll want to leave your cell phone and purse in the car. Besides this isn’t actually a dinner party at all, Nick and I share what he likes to think of as similar interests. Tomorrow will cater to a specific crowd.”

“What does that mean?” You watch as he gets up, carefully throwing his socks into the hamper and unbuttoning his pants. “What do you mean _similar interests?_ ”

“The guests in attendance all live a certain lifestyle.” He looks up, stopping to watch your reaction. “Dominant and submissive.”

“Oh,” you gulp, conjuring up thoughts of The Marquis de Sade. “But that’s kind of…us. That is similar, isn’t it?”

“Yes, that part is. But Nick takes it further. He’s deep into BDSM, sadomasochism, various forms of extreme sexual discipline. Most of it is well beyond my tastes.”

You digest this information, trying to imagine what kind of sights you’re going to see. “Why are you going if it’s not what you’re into?”

“Because he makes me a lot of money, millions over the last two years. And he likes to think of us as friends. So, once a year I go to his party and it keeps him happy. You are coming with me because I don’t want to be expected to participate in any of his little scenarios. If I’m there with someone I’ll have an excuse to abstain.”

“Okay.” You watch as he strips down to his boxers. His body is something to be appreciated, long and lean, the line of his muscles are easy to follow. He’s stronger than he appears under his suits and turtlenecks. “This isn’t a swingers type thing is it?”

“Not for us,” he confirms, disappearing into the bathroom as the shower turns on.  

You’re left unsure what that means and not entirely certain you want to find out.


	15. Fifteen

**Summary for the Chapter:**

> This chapter contains descriptions of bondage, public sex, genital piercing, ownership, whipping, the question of consent, a detailed non-consensual fantasy and anal sex.

Most Friday nights you’re chauffeured directly to Sam’s house, but tonight you went home after work in preparation for the “dinner party”.

You can hardly believe you’re going to meet Nick Luster, forget going to his house. Sam is rich beyond your imagination but Nick’s fortune dwarfs Sam’s tenfold.

Sam sent an outfit. You were nervous when you opened the box but it turned out to be nothing more than a strapless black dress that hugs your hips and showcases your breasts. There were no undergarments in his little care package and the dress has its own boning for support, so you take that as a clear instruction. He wants this dress to be the only thing you’ve got on.

-

“You’re quiet,” Sam observes as the car winds up a steep, tree-lined two-lane road.

“I’m nervous,” you admit, looking at where his hand is gripping your thigh. “This is out of my comfort zone.”

“It’s not exactly my cup of tea either,” he shrugs, glancing at his watch. “But who knows, you might see some things that interest you. There’s a lot of activities we haven’t tried.”

You shift in the seat, staring out the window as the car rounds a corner, revealing a massive house set up in the hills. There are thousands of twinkling lights flanking the driveway as you pull up to the main entrance. Sam gets out, offering you a hand and then tucks it over his arm as you walk toward the house.

Just inside the door is a metal detector. Sam steps to the side and a security guard ushers him around, as you are instructed to walk through it. It appears he’s above all this, but you certainly are not. Sam watches you stoically as you walk through the detector and then a man steps forward to pat you down. Once you’ve proven you’re not carrying anything on you, Sam directs you to an ornate table manned by a beautiful blonde who smiles wide as you approach.

“Mr. Winchester, it’s so good to see you again. You’re all set but your guest will have to sign a non-disclosure.”

“Really?” You turn to Sam, nerves stirring in your stomach.

“It’s nothing.” He leans in, one hand at the small of your back. “It’s just to ensure you won’t speak about anything you see or hear inside.”

The blonde leans forward, sliding an iPad and a stylus across the table. “Please sign here. Mr. Winchester is correct. I’m sure he’s explained everything. It simply states that you will not disclose any details of the night, such as any high profile guests you might encounter.”

“This is nothing new,” you mumble, bending over the table.

“Would you like a ribbon for your guest, or will she entertain this evening? Perhaps something more exotic?” The woman asks Sam, showing him a display case with ribbons of every color of the rainbow.

“Red,” Sam responds without pause.

“Here you go. I hope the two of you have a wonderful evening.” She hands him a silky red ribbon and moves her attention to the next guest.

“What is that?” you inquire as he ushers you further down the hall.

“Turn around.” He spins his finger as you turn your back to him. Reaching in front of you he places the ribbon around your neck and you lift your hair out of the way for him to tie it in place. “The color of the ribbons signify what you’re here for. White means available for use by anyone, no need to ask first. Many women here have multiple colors. White and yellow ribbons are a person who’s available for anal sex. You’ll see the whole spectrum tonight.”

“And red?” You touch the ribbon that’s fixed like a collar around your throat.

He turns you around, adjusting your hair as his eyes dart up from your neck. “Red means owned and unavailable.”

“Thank God,” you breathe and he chuckles, slipping a hand behind your back. “You won’t leave me alone here, will you?”

“No,” he snorts, his hand sliding over your hip. “Not tonight.”

At the end of the hall are two doors, twice normal height. They swing open as you approach and you enter what appears to an enormous solarium. There are the same twinkling lights from outside hung from the beams. The walkways and walls are lined with exotic plants.

The architecture is breathtaking but you immediately focus on two things. The first is a statuesque woman with the body of a goddess. She’s stark naked with tiny sliver clamps on her nipples, holding a tray of champagne.

There are several dozen people milling around. Some of the women are dressed like you, but others are in lingerie. One woman is wearing an array of ribbons around her neck and is completely nude save for a thin collar and a chain that’s held by an older, portly man.

“Holy shit,” you whisper, unconsciously moving closer to Sam. “This is like…something out of a book.”

“This is just the appetizer,” he sighs, walking the two of you to the other side of the room. “You’re going to see a lot of new things tonight.”

You stay close, following him into the next room. There’s a long dinner table set up, big enough for fifty guests and in the middle are nude women laid out as the guests sit drinking and talking as if there’s nothing going on.

“I’d like a drink.” You speak up, trying to cover your nerves. All he has to do is raise a hand and a woman appears to take your order. In record time you’re holding a double shot of vodka.

The lighting is dim and the crowd is milling around but you glimpse a scene in the corner of the room. There’s a man seated in an armchair, he’s smoking a cigar, head tipped back while a naked woman on her knees is enthusiastically sucking his cock.

“What do you think?” Sam asks, sipping a glass of what you assume is club soda.

“I think I’m definitely not an exhibitionist. I mean, I guess I am to some degree, but not like that.” You drink your vodka, unable to look away from the blow job in progress. “Is that something you would want?”

“I have no interest in an audience,” he quips, looking around.

“ _Sam Winchester!_ ” A jovial voice announces from behind you. Turning you find none other than the gregarious Nick Luster standing in a bright orange velvet suit. He opens his arms as if he expects Sam to embrace him and shakes his head, closing his eyes in dramatic flare.

“Nick,” Sam smiles, offering a hand and Nick takes it with a vigorous shake.

“It’s so good to see you, my old friend!” Nick pats Sam on the shoulder, his eyes falling to you. “And who do you have here? A plus one? What a novelty…”

“This is Y/N,” Sam’s arm curls around your waist, pulling you forward and into his side at the same time. “Y/N, meet Nick.”

“It’s very nice to meet you.” You bow your head awkwardly, somewhat star stuck.

“It’s my pleasure,” his eyes fall over your body, cocking his head to the side. “Red? How boring.” He rolls his eyes. “You bring us this luscious little creature but you’re not willing to share? Disappointing.”

“No,” Sam’s eyes narrow, his fingers digging into your hip bone. “She’s mine.”

This environment is all about dominance, a room full of powerful men and submissive women. Sam’s making it clear where he falls on the food chain.

“Well, at least we get to admire her from afar.” He examines you one more time before calling over a server and receiving a fresh cocktail. “Follow me. This is just the fluff, the good stuff is downstairs.”

Nick leads the way, stopping to greet his guests as he moves through the crowd. The man has mastered showmanship, you’ll give him that.

“Sam,” you whisper, watching Nick with interest. “Is he…gay?”

“No, just flamboyant.” Sam gulps down his drink, setting the empty glass on a table and grabs your wrist to pull you along behind him.

The two of you follow Nick through the growing crowd and down two flights of stairs into what you assume used to be a vast, underground wine cellar.

To your right, there’s a woman strapped to a table. Her arms and legs are each in restraints and she’s blindfolded with a ball gag in her mouth.  There’s a table beside her with all manner of toys laid out, dildos of varying sizes, clamps and whips. Multiple men surround her, groping her breasts and fingering her pussy.

“Did someone bring her here or is she part of Nick’s show?” you whisper unable to look away.

“It’s hard to say.” Sam watches for a moment, tilting his head before moving on.

The next sight you come upon is arguably the tamest thing you’ve seen all night. It’s a woman in lingerie sitting spread eagle in a chair. She has one hand inside her panties, touching herself as she moans and wiggles in pleasure.

A couple walks up beside you, the man is nothing special but the woman is gorgeous, tall and lithe, like something off a runway. You look at her neck, but she’s not wearing any ribbons.

“What about her?” Your interest is piqued. “She doesn’t have any colors.”

Sam leans down so that his lips brush at the shell of your ear and he speaks quietly. “That means anyone here is welcome to do anything they like to her. No limits.”

You shiver at the feel of his breath on your neck.

“What do  _no limits_  mean in a place like this?”

“I’m not sure you want to know,” Sam contends. “Things that would give you nightmares, I’m sure. Come on, let’s keep moving.”

You walk on further coming to the next set up and gasp the moment you realize what you’re watching. There’s a woman bent over a sawhorse. Her arms around bound in front of her, her entire head is encased in some kind of mask. But what takes your breath away is the man whipping her without mercy. Her buttocks are striped with blood as he brings the leather down over her ass again and again. What’s most disturbing about the scene are her muffled screams from inside the hood.

“Can we move on please?” You turn your head away.

“Sure,” Sam doesn’t seem phased at all, that familiar arm around you, guiding you away.

You pass a woman who’s laid out on an examination table. Her feet are in stirrups and her hands in cuffs at her side. There’s a man with rubber gloves, pinching her nipple with what appears to be metal forceps as he holds up a long needle.

“Oh my God,” you breathe, watching in a combination of horror and fascination as the woman has her nipple pierced right before your eyes. She moans loudly, arms tugging at the restraints, hips squirming in place. It’s not a cry of pain, or rather not exclusively pain. There’s pleasure in this for her, you can tell by the way her body is writhing.

“She’s exquisite isn’t she?” Nick Luster is suddenly beside you, staring at the woman on the table, shaking his head in appreciation. “Watch this part.”

The man prepares her opposite nipple, clamping and then getting the needle ready. You watch, slinking into Sam’s side as her second nipple is pierced and she has what appears to be an orgasm at the same time. You’ve got an unobstructed view of her pussy as it tightens and contracts, her legs trying to close but the stirrups hold them in place.

You’re simultaneously uncomfortable, a little queasy, and slightly turned on all at the same time.

The man at the table moves between her legs bringing the forceps with him and you turn to look at Nick. “He’s going to…”

“Pierce her clit? Of course. It’s the cherry on top.” He grins, chuckling at your shocked expression. “Would you like to have a turn on the table? Pierre does great work, there are a half dozen women on the list for this evening but we can fit you in.”

“No,” you mutter, looking to Sam who’s watching the interaction between you and Nick with his trademark non-expression. “I don’t want to see this.”

“What a wholesome little thing she is.” Nick eyes you up and down as you feel Sam’s fingers close around your arm just above the elbow.

“Yes, she is. Please excuse us, Nick. We’ll be back in a while.”

“No worries,” he calls out with a shit eating grin. “Feel free to use anything you like!”

Sam pulls you down the far hallway that winds off, leaving the bustle of the party behind.  

“Was all that…” you pause, searching for what you truly want to ask. “Consensual?”

“Of course,” Sam quips. “You like to be spanked, others have more extreme limits.”

You think about this, and how unphased he seems by everything you just witnessed. Things you’re going to think about for weeks to come, images that are seared into your brain.

“Are those things you want to do to me?” you ask, concerned that perhaps Sam’s expectations are far beyond anything you imagined.

“No.” He stops at a shut door at the end of the hallway, opening and ushering you inside before closing and locking it. You’re in a huge, ornate bathroom, big enough that there’s a sitting area with two chairs and coffee table. He turns to you, reaching down to pull your dress up over your hips, exposing your bare pussy. “Sit here.” He backs you up until your naked ass meets the cold marble of the counter. “Spread your legs.”

“But there are other things you want?” You dig deeper, watching as he wanders to the chair and takes a seat, his eyes locked on you. You follow up the question by hopping on the edge of the sink, lifting your knees to open your legs for him.

“I have no interest in inflicting pain on you if you’re not getting pleasure from it.” Sam clarifies, palming his cock through his pants. He’s hard, thick and bulging through his slacks.

“But it turned you on?” you ask, watching him watch you.

“Some of it,” he clarifies, unbuckling his belt, sliding down his zipper and taking his cock into his hand. “You liked it too.”

His eyes drop to your pussy and you touch yourself lightly in confirmation. It’s true, you’re wet. Blushing you bite your lower lip, watching him stroke himself.

“I think it’s the idea of those things that I like. I’d never want you to actually fuck me in front of someone else, or hurt me like that…but I enjoy the fantasy of it.”

“Touch yourself, rub your clit,” he instructs, lazily stroking his cock as if you aren’t in a bathroom at Nick Lusters house.

You do as he says, using your middle finger to gently stroke your own clit, wiggling from side to side and moaning softly. He was right, you are turned on, more than you care to admit.

“I could make you suck my cock in from of them,” Sam offers, his voice low with self-restraint. You look up, blinking as you stare him down. “I could march you back out there, tell you to get on your knees and choke on my dick. And you’d do it, wouldn’t you?”

“Yes,” you nod, mouth opening in a soft gasp at the thought of that kind of humiliation.

“Did you see anything out there you do want to try?” he asks, his gaze never leaving where your fingers are working between your shaking thighs.

“The restraints,” you admit, dipping a finger into your own slick. “The cuffs, I’d be okay with you tying me up like that. And the ball gag, you have one but we haven’t used it.”

“I’ll make both those things happen.” His eyes flick up for a moment, watching as your face twists in pleasure. “I want you to tell me one of your fantasies. Something you’re embarrassed by. A fantasy that you’ve never admitted to anyone.”

Despite the fact that you’re masturbating in front of him, the concept of admitting your deepest desire makes your whole body flush with shame. But the moment the command leaves his mouth you’re already sure of what you’ll share.

“There’s one thing I think about…” you shift, starting to become uncomfortable with the position.

“Come here,” Sam gives his cock a final tug, patting his knee.

You shudder, pulling your hand away from yourself and nearly stumbling across the room. When you try to crawl into his lap, he stops you. Two wide hands curl around your hips, turn you around and ease you backwards onto his lap.

“Up,” he grabs his cock as you lift yourself up, notching the head in your pussy. “Take it all.”

“Fuck,” you whimper, sinking down until he’s inside you to the root. Your legs are bent and he slides a hand under each knee, forcing your legs to fall lax on either side of his. There’s no leverage like this, all your weight is keeping you impaled on his cock. One of his hands curls around your chest, urging you to lean back until your head is resting on his left shoulder, his jaw against your temple.

“Just like this,” he murmurs, one hand sliding inside your dress to grab your breast, the other sliding over your belly as he starts to make soft, slow circles around your clit.

“Shit, Sam,” you wriggle, feeling the head of his cock right on the edge of too deep.

“Now, tell me about your fantasy.”

_Fuck._  You take a breath, trying to think while you’re stuffed full of dick and he’s methodically rubbing your bud.

“I imagine that I’ve done something that makes you mad,” you start, your entire face burning hot, thankful he can’t see it. “You’re so angry and you grab me hard enough that it hurts. We’re in the living room, or the kitchen when it starts, and you grab my hair and walk me down the hall to the bedroom with my arms pinned behind my back.”

“How hard am I pulling your hair?” he asks, his jaw moving against the side of your face as he speaks.  

“Hard, it excruciating.” You nod. Sam begins to slide two fingers along either side of your clit, pressing slowly together and you whimper, tightening around his cock.

“Continue.”

“When we get to the bedroom you force me onto the ground and tear my clothes off.”

“Are you scared?”

“Yes, I’m scared because you’re so rough but I’m turned on by it too. It’s making me wet and I’m ashamed that you’re going to find out..”

“Keep going,” he urges, dipping his fingers into the slick of your cunt and going back to stroking your clit with the long, even press of his fingers.

“You force me onto my belly. At one point I try to fight you, but I can’t because you’re too strong. Then you spank me. It’s brutal, harder than you ever have before and I’m crying it hurts so bad. But then you check my pussy and find out I’m really wet. That makes you even more upset.”

“Why?” he inquires gently, his unassuming tone the polar opposite of the fantasy you’re describing to him.

“Because you tell me that I deserve to punished and I’m not supposed to enjoy my punishment. You call me names, a whore, a slut. And then…” You stop, moaning loudly as he grazes directly over your clit. “Then you make me ask you to fuck me up the ass.”

“Do I?”

“Yes. It’s painful. You make me take your cock so deep. I beg you to stop, but you won’t, because I need to learn my lesson.”

“When you’re begging me to stop, do you really want me to?” he whispers, gently pinching your clit.

“No,” you pant, feeling the stretch of his cock in your pussy. “I like it when it hurts. I enjoy it even though I don’t want to. When you cum in ass, I cum too. I try to stop it but I can’t.”

“What happens then?” he inquires, squeezing your breast with his free hand.

“Nothing, that’s when I cum in the fantasy and it’s over.”

He chuckles, shifting under and inside you, making you rock forward.

“Sam,” you start, breathing picking up as his finger moves faster over your clit. “You know that I don’t-”

“Do I understand that you don’t really want me to hurt you or fuck you without your consent? Of course. That’s why it’s a fantasy,” he explains, turning his head to nip at your jaw. “You have to enjoy it, for me to enjoy it. It’s why you’re perfect for our arrangement. We have the same preferences and the same limits.”

“God,” you squirm, feeling the heat of his body behind you. His cock feels unfathomably thick tonight and he’s working your slit faster now, his touch growing insistent. “You’re gonna make me cum like this.”

“No, you’re not,” he corrects you, his fingers still moving causing you delicious torture. “What’s the rule for this weekend?”

You whimper, your fingers curling into the arms of the chair. “I can’t have an orgasm unless I have your cum in my mouth.”

“And do you have my cum in your mouth?”

“No,” you confirm, clit throbbing with each heartbeat.

“That’s right,” he scolds, pulling his hand away right before giving your pussy a nasty slap that makes you yelp. “And right now I want to cum in this warm, tight little pussy. Doesn’t look like you’re cumming any time soon. Get up. I’m going to fuck you.”

He practically lifts you off his dick. You stand up on shaky legs, feeling him behind you. He bends you forward until your palms meet the coffee table. He slaps your thighs apart, widening your stance, then slides his cock back into your pussy and fucks you fast and hard.

“Oh my god,” you moan, biting your lip to keep from screaming. At least you can’t cum like this. While it feels amazing there’s nothing touching your clit and the angle isn’t right for your own pleasure, so you enjoy the sensation of him taking you for what it is.

It’s only a few minutes before he speeds up to a fever pitch. There’s the wet sound of your pussy taking his cock and the smack of his hips meeting your ass. His breath goes choppy, he thrusts harder and faster and then he cums with a long, low grunt. Your hips hurt where his fingers dig into flesh, holding on for dear life as he spills inside you, spurting thick until he’s finally satisfied.

“Fuck,” he heaves, both hands grabbing your butt cheeks. “Shit, that was good.” He slowly pulls out, standing back to get a good look at you before removing his hands. You start to stand up, but he places a hand on your lower back to keep you in place. “Don’t move. You’re a mess.”

Bent over the coffee table with his load running your thighs, you watch as he moves to the sink to get a towel and wipe his cock off. Then he rinses it out, and coming back to you, moves behind you to clean your thighs and aching sex. Once you’re clean he reaches back between your legs, thumb pressing lightly over your clit several times before he’s done.

“Stand up.” His hand curls around your bicep, helping you into a standing position. Then he crouches down to pull your dress back into place. When he stands up he gets one look at your face and chuckles, walking you to the mirror.

You look like you’ve been fucked six ways from Sunday. Your hair is a mess, eyes watering and lips swollen from biting into them. You’re sweating, cheeks flushed and still breathing fast.

There’s no mistaking what’s just happened to you. Everyone will know.

“I guess this is the one place we don’t have to worry about someone knowing I fucked you in the bathroom.” He grins, standing tall behind you, admiring his handiwork. “How do you feel?”

“Horny,” you admit, pressing your lips together as you turn to face him. “Are you sure you don’t want a blow job? Because I’d really like an orgasm.”

He laughs out loud, a genuine smile overtaking his face.

“You’re going to have to wait.” Reaching out he places a hand on your shoulder, pulling you closer. “There’s still more of the party and I haven’t decided when I’m going to end your misery.”

“Well, that’s comforting,” you snort, grinning despite the fact your entire body is vibrating.

He tucks a lock of hair behind your ear, finding your eyes with his. “Come on, let’s get you another drink and find Nick before he comes looking for us.”


	16. Sixteen

You follow Sam down the labyrinth of halls, back through the various women who are still performing. You’re relieved to be back upstairs, up here it seems to be a tamer crowd. More nudity and blow jobs in the corner than pain and strange kinks. You can handle that.

“I hope you two enjoyed yourselves.” Nick appears in front of you like a slithering snake, his eyes taking stock of your appearance as a smile spreads across his face. He turns to Sam with the proud expression of a doting father. “She’s even more delicious when she’s freshly fucked.”

You unconsciously bring a hand up to your face, feeling your already flushed cheeks. Sam’s brow ticks, the hand above your elbow tightening its grip in response.

“I think _she_  can hear you.” Sam leans toward Nick. “But that’s the point, isn’t it?”

“There’s nothing wrong with casual observation,” Nick chuckles good naturally, winking at you. “You don’t mind, do you, my dear?”

“No,” you answer, lifting your head high. Everyone in the room is here for the same thing. And comparatively, what you and Sam have going on is pretty vanilla. Acting like a shrinking violet gives Nick the power, and you’re only comfortable relinquishing your power to one man. “I don’t mind as long as Sam doesn’t.”

Nick cocks an eyebrow. “What a perfect little thing you must be. Are you sure you don’t care to share, Sam? We’re all friends here.”

“No,” Sam shakes his head, thoroughly unamused. “Not if you’d like us to remain friends.”

“My, my,” Nick pats his belly, looking between you. “Have we finally found your Achilles Heel?”

Sam’s response is immediate, his demeanor shifting on a dime. “What is that supposed to mean?”

“Nothing.” Nick can read his response just as well as you can. He’s said too much and once that line is crossed with Sam, it’s hard to retreat. “Nothing. You’re always so serious. Lighten up, have a drink.”

“It’s been a pleasure Nick, but it’s time for us to go,” Sam snips, pulling you along with him.

Nick calls something after you, but you don’t hear him. All you can focus on is Sam guiding you away from the party, toward the front hall.

There’s no misreading this.

You can’t help but feel somewhat hurt by how strong his response was to Nick insinuating he has even a minute amount of affection for you. Had he not responded at all, you would have assumed his indifference, but now he seems almost angered by the implication that perhaps your arrangement is something more than  _contractual satisfaction._

Within five minutes you’re back in the car. Sam doesn’t say a word, just stares out the window as the black of the night settles in and the lights of the party fade into the distance. He’s silent the entire ride back to his house, doesn’t even offer you a hand to exit the car, just lets you scamper behind him, unsure what your next move should be.

Should you offer to leave? The truth is your confidence is shaken, how could it not be?

“Sam,” you start, following him into the kitchen.

“You’re not going to talk for the rest of the night. Do you understand?” He turns to you, eyes practically on fire. When you hesitate he takes a step closer. “No words, _do you understand me?_ ”

You nod  _yes_ , looking sideways to the counter, anything to get his eyes off yours.

“Clothes off, take a shower. I’ll be waiting in the living room.” And with that, he turns and walks away.

When this first started, back when he called you to his office and told you to sit on his desk and open your legs, you felt like this. The swell of so many emotions that you could hardly isolate just one. That’s how you’re feeling now, except there’s something new added to the mix. An unsettled feeling that’s stronger than everything else.

You strip down, leaving your dress in a puddle on the tile of the kitchen floor, and shower as instructed. Once you’re clean and dried, you walk nude back to the living room where he’s standing, one hand in his pocket, the other holding his phone.

“On your knees, back against the wall,” he gestures, setting down his phone and unzipping his pants.

It’s impossible not to feel the shift in his demeanor. This is the man you first met, the one that ordered you to take off your panties in the elevator and carry his bags like a servant.

“Hands behind your back, open your mouth.” And with that, he fucks your mouth for the better part of an hour as you willingly gag on his cock. While you are worried about this change in the dynamic, it’s also a turn on. The two of you have become more familiar with each other, you know what to expect from him…but not tonight.

Tonight he slips back into the man who scared and excited you nearly every time you were in his presence. Every touch is hard and demanding, every order given expectantly. And you comply with everything, just as eager to please him as the first time. You trust that this is just temporary and that things will return to the new normal soon enough.

-

There’s only one explanation, he must feel what you do. At least that’s what you hope.

And what do you feel? You’re not entirely sure, but it’s something. Something more than just sex.

The very notion seems insane, you and Sam Winchester. But there’s this undefinable thing growing between you. You know it and so must he.

And just as sure as you are about these feelings, the doubt creeps in. Sam isn’t the kind of man that has relationships. Hell, the guy doesn’t even have a friend. You’re crazy if you think that he’s going to make an exception for you.

You’re misreading the situation, you have to be.

But what if you aren’t?

Bouncing back and forth between both possibilities you decide on a small gesture. A little offering to test the waters. After all, what do you have to lose?

 

**The Following Sunday**

Standing in Sam’s living room you stare at the paper tickets in your hands, regretting the choice to buy them. It’s a ridiculous idea, a man like him doesn’t want to do something as plebeian as a planetarium.  

He’s been in a terrible mood all weekend. He’s barely spoken to you. It’s been two and a half days of nothing but sucking cock, getting spanked so hard you can barely sit down and taking his cock from behind while he nearly pulled your hair out.

The weekend has come to an end, just as it always does. The wind down that never fails to leave you unfulfilled.

Now, you’re waiting silently for him to send you off. It’s a tradition. After you fuck for the last time, he showers and changes before walking you to the door like a gentleman in some dime store novel. Tonight you can still feel his cum between your thighs while you look around his whitewashed house.

Whatever’s gotten under his skin has made him even more cold and distant than usual. You know you should hide the tickets before-

“What do you have there?” Sam inquires, clad in a fresh shirt.

“It’s nothing.” Looking up you feebly attempt to remain casual.

“Doesn’t seem like nothing,” he presses, stepping and holding out his hand. “What is it?”

“It was a stupid idea,” you wait for a beat, before laying the tickets in his hand.

He looks at you skeptically and then down at the tickets, “The Museum of Science Planetarium?” He lifts an eyebrow. “Were you planning on us getting high and watching a laser light show?”

“No, it’s not, it’s-” you look at his utterly impatient expression. He’s already annoyed with you. “It’s the Northern Lights Experience. You said-”

“I remember what I said.” His eyes go soft, a look he gets from time to time, his expression softening as he stares at you and then the shift. His jaw sets, eyes hard again. “I think it’s time we rethink our arrangement.”

“In what way?” You perk up, trying to get a read on him.

“We’re not going to see each other anymore.” Sam says the words like he’s explaining what you’re about to have for dinner.

“What do you mean?” You inch closer, studying his deadpan stare. He can’t mean what you think he means.

“Our time together is over. Permanently.” He blinks.

“What?” You’re breathless, heart falling into your stomach. “Why?” you sputter.

“Because,” he sighs, pulling off his glasses. “I’m done with you. I’m bored. It’s time to move on to something new.”

_Something new._  You know exactly what he means,  _someone_  new.

“You’re bored with me,” you repeat to yourself, staring at the carpet, swallowing hard. You won’t cry in front of him. It’s no doubt what he expects but you will not give him the satisfaction. “So that’s it? Just like that. We’re over?”

“It’s time. It has been for a while.” He picks up his phone, tapping the screen. “I’ll have my driver take you home.”

“Why did you even spend the weekend with me?” While you can hold back tears you can’t cover the pain in your voice.

“I wanted to fuck. I had a stressful week and I needed some tension relief.” He responds matter of factly. “There’s no reason for us to interact at work. We shouldn’t have to see each other. You’ll be able to keep your job.”

He’s being cruel, this is his specialty. His true colors showing through. All you can see are the tickets in his hand. Those tickets that were so much more than tickets, the symbolic gesture you wanted to give him in return after your birthday. An offering, a chance for something more. Here you were planning, wishing for things to move just little closer to affection and he’s been planning how he was going to fuck you one last time before he threw you out with the trash.

Sam Winchester is a cold son of a bitch, you should have known this was how it would end. Taking a breath you stand up tall, holding your chin high, eyes blinking cold and expressionless. After all, you’ve learned from the master.

“I think it’s probably for the best.” You smile as if you’re the one letting him down softly. Your mind is swirling, but right now all you know is that you want to hurt him, really hurt him. “I mean, you always made me cum but the orgasms have been a little…softer lately.” His brow twitches, nostrils flaring as he looks at you like he wants to wrap his hands around your neck. You doubt anyone has ever spoken to him like this before. “I’ll be alright. Maybe I’ll give Max a second chance. I do love assholes.”

And with that, you turn on your heels and walk out of his house. You hold it together until the car pulls out of the driveway. For a moment you can’t think, can’t breathe. How has your life become this? A break up that was never really even a relationship at all. You were part of a contract, it was just sex all along and you should have known.

Tears fall as his house disappears behind you and the car drives back toward the city. Toward the next chapter of your life. A life without Sam Winchester.

-


	17. Seventeen

**One Month Later**

“Hello, earth to Y/N.” Millie’s hand is waving in front of your face as you snap to attention. “Jesus, what is going on with you?”

“Nothing.” You shake your head, tapping the mouse to wake up your computer. “I’m just tired.”

“You don’t have to tell me, but don’t assume I’m an idiot.” 

You’ve shared a little, she knew you were seeing someone, now you’re not. But you’ve never gone into details. She guessed once that your mystery weekend guy was some married man with a wife and kids. You let her live with the assumption. It’s easier that way. 

Millie tilts her head, eyes flicking to Lexi’s empty desk. “Did Lexi tell you she’s working on some super secret project for the boss man?”

You want to throw up. Of course she is. 

“She told me,” you confirm, typing in your password twice before getting it right. 

“What do you think it is? I mean I love the girl, but she’s not the sharpest tool in the shed.” Millie looks at you, frowning in concern. 

You have a pretty good idea what kind of special project Sam’s assigned her to, the same kind you worked on. He was bored fucking you so he moved on to someone younger, firmer and dumber. As much as you try to fight it, your mind can’t help but conjure up images of her on her knees sucking his cock. 

“Seriously, are you okay?” Millie places a hand on your shoulder and you flinch, looking up at her. “You’re all over the place.” 

“No,” you shake your head, sitting back in the chair. “I don’t think I want to work here anymore.”

“Seriously?” Millie hunches down, getting close to whisper, “did Max do something again? Is someone bothering you?”

“No, he’s actually been really apologetic after he was put on his corrective action plan,” you snort. “I’m just fucking done. This place is a black hole and I need to move on.” You look at Lexi’s empty seat. “I’m gonna go talk to Pepper and put in my two weeks. Then I’m gonna let you take me out and get me drunk.”

**\--**

After a few shots of tequila, you sit at the open window of your apartment, sipping a bottle of water and watching the city lights at night. For the better part of a year, life was focused around Sam, when you’d see him next, what would happen. Now that excitement is nowhere to be found and you're left with the realization that you’ve let the other parts of your life fade into the background. There’s a kind of emptiness that you’ve struggled to fill, a void that you’re learning to live with. 

Above all else, you feel foolish. While you want to feel betrayed, you simply can’t. He was always up front. He told you time and time again it was nothing more than sex. But your logical mind and your heart aren’t always working together. Developing feelings for someone like Sam Winchester was bound to end badly, you knew that from the start.

If nothing else, Sam taught you a lot about yourself. Sex with him was eye-opening. He showed you how to openly desire all the things that you hid for so long. Not only do you know what you like, now you know how to ask for it and you’ll never be ashamed of what turns you on again. 

It’s been one hell of a rollercoaster but it’s time to leave. Not just W & S, but Boston as well. It’s time to start over. In a couple of weeks, you’ll be in Chicago, a place where you know no one and no one knows you. It’s for the best, here your memories are haunted, little pieces of Sam everywhere. At least you learned a lesson. 

As you lay down to go to sleep you glance at the bedside table. There’s a small vibrator in the drawer. You’ve tried to masturbate several times since your final goodbye but you can’t quite get there. All your fantasies somehow morph into Sam at the end and it pulls you right out of the moment. Perhaps more distance will help you get back to normal. 

You fall asleep dreaming of a new life, somewhere far, far away. 

 

**Two Weeks Later**

Juggling a comically tall stack of folders you head to the conference room. 

You’re late for your last meeting as an employee of W & S. It’s your project hand-off, going over all your active cases with Pepper and Millie. Only a few more hours and you can kiss this place goodbye for good. 

It’s as you open the door and flick the light switch, you’re met with a chorus of happy voices.

“Surprise!” 

You jump back, breaking out into a smile at the room full of colleagues in party hats. There’s a sheet cake in the middle of the table with _We’ll Miss You!_ scrawled across in blue frosting. 

“You scared the shit out of me!” You laugh, dropping the files onto the table. 

“That was the idea,” Pepper smirks, sliding a paper cup of punch across the table. “It’s not a surprise unless you shit yourself.”

“Honestly I didn’t expect this. I didn’t think anyone would care that I left,” you confess, looking at an envelope with your name written across it. 

Millie is already cutting the cake, handing you the first piece. “Are you kidding, we all love you. It’s gonna be boring without you. Don’t get too excited about your gift, it’s only an Ikea gift card.”

“I never thought I’d say this,” Pepper leans in, dipping her finger into the frosting on your plate. “But I sure wish you were staying, Lexi is a nightmare.” You both look up at Lexi who’s babbling on in the corner of the room clad in a skin-tight pink dress. “I long for the days of your slow walking and crappy notes.”

“Good to know I’m appreciated in hindsight,” you force a smile, trying to focus on anything other than thoughts of Lexi and Sam. 

There’s a faint, repeating noise in the distance, it’s out of place but you’re not really paying attention. 

“Hey,” Max slides in beside you. Millie sighs but backs off. “I just wanted to say I’m sorry, for _you know_ , saying that stuff about you. I was a dick.”

He has been making an effort, there’s a subtle hint of that nice guy you met before he turned into a full-fledged bastard. 

“Yes, you were.” You roll your eyes, offering him a smile. “I forgive you, but only if you don’t do it to anyone else again.”

“I swear,” he nods, a hand over his heart. “Lesson learned, I-” 

He pauses to listen to the popping in the distance. The room falls silent. 

“Is someone setting off fireworks?” Pepper stands up, moving toward the window. 

“That’s not fireworks,” Tim Bellamy from accounting stands up, walking to the door of the conference room and looking out into the hallway. “That’s gunfire.”

“What are you talking about?” Your heart speeds up to gallop, a low simmer of panic setting in. Right on cue, all the lights shut off, the whirl of the air conditioning stops. 

There it is again, closer than before. It sounds like it’s coming from a few floors down. 

_Pop_

_Pop_

_Pop_

_Pop_

“Someone’s shooting,” Millie whispers, looking to you with eyes the size of saucers. 

“Security will stop whoever it is,” Pepper’s voice is broken as she wrings her hands together, staring at the open door. 

“What do we do?” You look at Tim. You don’t know much about him, but you do recall that he’s a combat veteran, a Marine if you remember correctly. 

“We run,” he confirms, taking off his suit jacket and throwing it on the table. “If you're wearing heels, take them off. Get rid of anything that’s going to slow you down or make noise.” 

You reach down, slipping off your pumps, bare toes sinking into the carpet. You’re sweating now, listening to the burst of gunfire coming in rapid succession. For a moment it’s getting closer then there’s a break, silence. 

“Follow me.” Tim inches toward the door, peeking out into the hallway. “If you get out into the open don’t run in a straight line, zig-zag back and forth. Doesn’t matter if anyone’s shooting at you, make yourself a hard target to hit.”

“This isn’t happening,” Millies cries behind you, her hands on your hips. “Oh my god, this can’t be happening.”

“Quiet,” Tim turns back, looking at each one of you. “Stay silent. Follow me now.”

You trail after him down the hall, everyone moving in silence, grasping each other’s hands. The hallway opens up into a sea of cubicles. You’re headed toward the red exit sign at the other end of the room, it’s the door to the stairwell. 

Without warning the door slams open, hitting the wall with a thud. Millie yelps, Lexi screams from somewhere in the back. Trevor from IT comes sprinting toward you, sweating, in pure panic. 

“He’s coming!” He yells running past you in a sprint.

“Who’s coming?” Max yells. 

“Brent!” Trevor calls back, his voice faint as he disappears around the corner at the other end of the room. 

_Brent._

“Fuck,” you breathe, remembering the day he was fired, how it took multiple security guards to wrestle him out of the building. “Where do we-”

Your voice turns into a scream as Brent appears in the doorway. He’s holding some kind of huge rifle, the kind you’ve seen in movies as he jams in a fresh clip. He looks up spotting your group. 

“Run!” Tim shouts, stepping in front with his arms spread wide. 

Time slows down and you have a thousand thoughts at once. 

_You should have called your mom this morning._

_You’re not wearing matching underwear._

_You should have told Sam how you felt as soon as you felt it._

_You’re going to die on your last day here, you should have left last week._

_If you’d have gone to college, none of this would have ever happened._

There is an ear-shattering pop and Tim’s body jerks back, careening into you before he hits the wall and his knees give way. He’s clutching his stomach, blood pouring from a wound. You’re frozen in sheer terror, a scream erupting from your throat as Brent advances. 

There’s a shout from the other side of the room, a woman you’ve never seen before shrieks drawing his attention. There’s a spray of bullets in her direction and you watch in horror when she sinks behind one of the cubicles. 

Turning back to you Brent looks calm and focused as he takes aim and shoots off another round, hitting Max in the upper thigh. One more step and he shoots again, the bullet hitting Max’s chest and this time he falls to the floor. 

Brent is close now, his eyes narrowing as he hones in on you. 

“Please,” you whisper, shaking uncontrollably as you raise both hands in front of your face. There is no sight or sound, everything comes to a halt as you take a final breath.  “Please don't kill me.”

Brent just snorts, raising the gun and pointing it at your head. 

Sam comes out of nowhere moving with a speed and power that you would have never known he was capable of. He drives the heel of his hand up into Brent’s chin, snatching the rifle from him in the same move. Swinging the butt of the gun around he whacks Brent in the head hard enough that it makes a sickening _crack_. Blood begins to pour from the wound as Brent’s knees buckle and he collapses to the ground. 

With a series of methodical movements, Sam disassembles the firearm as if he’s done it a million times before. In ten seconds flat it’s laying in pieces on the carpet. He kneels next to Brent, patting down his unconscious body and pulling away two handguns that are tucked into his waistband. Sam takes those apart as well, leaving the pieces on a nearby desk. 

“Are you alright?” he asks and you realize he’s talking to you. You blink, your mind a blank slate looking from Brent to Sam who’s standing in front of you, one hand on each shoulder. “Y/N?”

“I think so,” you mutter, staring at him in disbelief. All that fear is suddenly gone and you’re numb, physically and emotionally, save for the nauseous feeling in your belly. You explain calmly, “I think I might throw up.” 

“That’s okay,” he cups your face for a moment, both hands under your jaw, giving you his undivided attention. “Are you hurt?”

You shake your head _no_ , turning away from him to vomit onto the floor. 

“Oh my God!” You hear Lexi’s high pitched shriek coming up behind you. When you look up she’s throwing herself at Sam, wrapping arms around him. “You saved us!” 

Sam just looks at you, his arms dangling at his side as she presses her head over his chest. 

“Ohmygod, ohmygod,” Millie’s arms are around you, trembling as she squeezes tight. Wiping your chin you heave again, the last of your stomach contents coming up. “You’re alright, you’re gonna be alright.” She keeps repeating, rocking back and forth as she strokes your hair. 

It’s not exactly soothing for you, but it seems to be what she needs, so you let her cradle you. 

The next few minutes are a blur. Every moment melts into the next. There’s a swirl of activity, police and swat officers swarming the room. Several people are talking at you but you can’t hear them, your ears are ringing and you’ve got tunnel vision. Someone moves you, there’s a hand on each arm and you’re walking but not sure where or how. 

The next thing you know you’re in Sam’s office, sitting on his couch. He’s standing near his desk and you’re surrounded by a dozen agents with ATF and FBI emblazoned on their clothes. 

The voices come in and out of focus. There’s a man sitting next to you, his mustache is untrimmed, creeping over his upper lip and for a moment it’s all you see. 

“Y/N?” he asks, leaning closer. “Can you hear me?”

“ _She’s in shock._ ” A female voice comes from somewhere in the background. “ _We have an ambulance on the way. We needed to get the critical cases out of the building first. We can have someone drive her-_ ”

“I can hear you.” You clear your throat, feeling like you’ve been shot with a tranquilizer. A hush falls over the room and you look from the man in front of you to Sam. “I don’t wanna go to the hospital. Please don’t make me.”

“Okay,” Sam nods, walking over and sitting on the coffee table in front of you. “She can wait until tomorrow, can’t she?” He looks at the officer next to you. 

“ _We don’t recommend it_.” Another voice answers. 

“I don’t want to be here anymore.” You look around at the strangers staring at you like a zoo animal. “Sam, I want to leave.”

“ _She shouldn’t be alone in this state. Once we have her emergency contacts we’ll send a car to take her home._ ”  

“That’s not necessary she’s going home with me.” Sam reaches out, squeezing your knee. “We can set up a time tomorrow afternoon for interviews.”

-

You sit in silence next to Sam as the car makes the drive to Newton. The world whizzes by as you look out the window, your mind a blank slate devoid of any real thought. Sam doesn’t say anything, you’re vaguely aware of him looking at you from time to time. By the time you reach his house, your mind and body are starting to equalize. You follow him into the house, looking around at the all too familiar surroundings. Nothing's changed since the last time you were here. 

Sam walks directly into the kitchen, opening up a cupboard and pulling out an empty trash bag. 

“Take your clothes off.” He instructs calmly. You snort, eyes widening, unsure of how he can even think that you’re going to comply with his commands- “You have blood on your clothes,” he explains and you feel instantly sheepish. “Undress and take a shower.”

You look at him, a combination of betrayal and exhaustion. There’s a lot you want to say, but instead, you pull your blouse over your head, then shimmy your skirt down your hips. He holds open the bag and you place both inside, then strip the rest of the way, peeling off your panties and bra. 

Naked, you pad down the hallway to his room, leaving the light off as you find the way to his shower and climb inside. You sit down on the tile under the warm water, pulling your legs up to your chest. You stay just like that until the water runs cold and you have to get out. 

When you finally get out, you halfheartedly dry off, leaving the towel on the hook and a series of wet footprints on the hardwood of his bedroom floor. 

Sam is sitting on the edge of the bed but stands up the moment he sees you. He must have used the guest shower because his hair is wet and he’s wearing a plain white t-shirt and blue and white striped pajama pants. 

You just stand there in the nude, staring at him, a million thoughts colliding at the same time. 

“Why am I here?” you ask quietly. You’re not sure if you want the answer, you’re still upset with him, raw over your last conversation. 

“Because I want you here.” He responds evenly. “You were traumatized and I-”

“I’m not the only one who was traumatized,” you interrupt. “I don’t see anyone else here.”

“No, you don’t.” He raises his chin, jaw locked in place. 

“How did you know how to do that? What you did to Brent, I’ve only ever seen people fight like that in the movies.”

“My dad,” he explains, running his tongue over his teeth under his upper lip. “Winchester 101.” 

“Right,” you nod, feeling water dripping from the end of your hair, down your back and over your breasts. “You’re a hero. You came to save us. Guess you’re not a total asshole.”

“I am a total asshole. I don’t give a shit about anyone else.” This confession comes out just as simple as everything else while you stare at each other. “I came for you.”

“Why?” you ask imploringly, stepping forward. “Why didn’t you come for Lexi, she’s your _special project_ now.”

“You think I’m sleeping with her?” He raises an eyebrow, letting out a humorless chuckle. “Well, that’s what I hoped you’d assume. I wanted to hurt you because _I am_ an asshole. I wanted you to move on. But I’m not fucking her. I have her reporting back me on Peter Kelson. He’s leaking information. He wants to fuck her, so he drinks too much and tells her more than he should and then she tells me. That’s all.” 

“I don’t understand you,” you sigh, defeated. “You said you were bored with me. You cut me out like I was nothing and now you’re telling me you put yourself in front of a bullet for me?” 

“I lied.” He shrugs, looking to the side before forcing his gaze back to you. “I was, _I am_ , uncomfortable with the way I feel about you. I want to be with you, I care for you. That’s not something I know how to do anymore. I gave up on that concept a long time ago.”

Your heart does a little skip in your chest, first the worst day of your life and now _this_. Whatever _this_ is.  

“You can’t just...do _this_. You walked away from me like I meant nothing to you.”

“I wanted you to hate me,” he confesses, eyes transfixed on yours waiting to see if you’ll bolt. 

“I did.” You shrug, stripped bare of pretense. There’s no room for anything to be left unsaid, not anymore. “I do, hate you. The way you treated me made me feel small...insignificant.”

“I know,” he nods, blinking twice, before looking at the floor to gather himself. “But you’re not.”

“I care about you.” You look down at your hands. “But how can you say that? You were going to let me leave. Let me move halfway across the country.” 

“You would have been fine.” He steps closer, face tightening in displeasure. “You were hurt, and pissed at me, but you would have moved on. I was going to let you go but I couldn’t let you _die_ , I couldn’t go through that again-” His voice wavers and he pauses, searching your face. “I make a shitty partner in every sense of the word. I’m selfish and impatient. I don’t like relinquishing control. I don’t like to talk about how I feel or my past. I’ll hurt you and you may end up hating me in the end...but I don’t want you to go. I want you to stay in Boston, to stay with me.”

“You haven’t apologized yet, apologized for hurting me like that.” You swallow, watching his jaw set wishing you could just read his mind. It would make this so much easier. 

“I’m sorry.” He implores and for the first time you see a side of him you would have not imagined existed. He looks vulnerable, sad and desperate, completely out of character. 

“Will you try?” you whisper, tears brimming in the corners of your eyes. “It’s one thing to say that you’re terrible at relationships but it’s another to accept it. You put so much energy and commitment into your work, Sam. Are you going to give me at least some of that? Because if you’re not going to try, then there’s no point.” 

“I’ll try,” he nods. “I give you my word.”

“Then I’ll stay,” you murmur as his hands cup your face, sliding along either side of your jaw. 

He leans down to kiss you, lips meeting gently for the first time. As adept as he is in the bedroom, you wonder if he’s kissed anyone like this since his girlfriend all those years ago. He’s hesitant, the gentle press of his mouth to yours growing more passionate as you slide your tongue forward. That first kiss grows, hands pulling and grabbing, anything to be closer to one another. 

He’s naked before you hit the bed, whipping his shirt over his head and stepping out of his pants before he picks up and spreads you over the mattress.  For all the sex you’ve had, all the spanking and groping and sucking, you’ve never felt him like this. The heat and heft of his body take your breath away. This much skin on skin is like a drug as you wrap your legs around his waist, holding him tight as he kisses you long and deep. 

His cock is thick and hard, poking your thigh as you whimper and moan underneath him. Your fingernails dig into his back holding on, desperate to have him just like this. You could drown underneath him in this bed and die happy here and now. 

You’re both making up for lost time, his mouth sealed to yours as he moans against your lips, pulling back only long enough to suck in a breath before tasting you again. 

Spreading your legs wide you watch as he notches of the head of his cock in your pussy. That first push inside makes you gasp as he stretches you open. Your mouth opens wide against his as he slides home, filling you to the root. 

“Fuck, Sam,” you whine, fisting one hand in his hair as he strokes in and out, setting an easy pace that’s far from the usual. “You feel so good like this.”

“Gonna make you cum so hard,” he mumbles against your lips. Grabbing a fist full of hair he tugs your head back, slowly pulling your neck taught. “Look at me.”

“I am,” you promise, eyes opening as his cock moves inside you. It’s a full feeling that sends a tingle up your spine and then fans out in all directions. While you can’t orgasm from just this, the stretch of his shaft feels incredible. For a long time, he fucks you just like this, the weight of him pressing you down into the bed, his chest laying over your beasts, and his mouth sealed to your lips. 

While he’s not exactly gentle, he’s also not as rough as he has been in the past. His breath is hot as he buries his face in your neck, grunting and panting with every stroke. Tonight is about pleasure and connection and you’re practically humming on every level as the world fades away and only this moment exists. 

Sam props himself up on his arms, breathing heavy as he rocks strong and deep. One hand cups your breast, just holding you as you stare up him, his hair hanging down, swinging with the movement of his body. He dips down for one more kiss before lifting himself up enough to wedge his hand between your bodies in search of your clit. His mouth seals shut in concentration as he thrusts steadily, making gentle sweeps over your bud. 

It doesn’t take long, you’re already drenched in pleasure and with the addition of his touch, you swell with satisfaction.

“Can I cum?” you pant, mouth falling open as you hold back, waiting for his permission out of sheer force of habit. 

“Yes,” he gasps, pressing forward, holding his cock deep and rubbing your clit and you come undone, clenching and pulsing around him. 

“Oh God,” is all you can muster, twitching and jerky underneath him. 

He knows what you like, you prefer when he keeps his cock buried in your cunt as you cum instead of fucking you through it. It makes everything better, perfectly stuffed and stretched as you pull him inside, muscles tightening with each wave of pleasure. 

He waits for you to come back down, letting you fall limp as he picks up the pace fucking you quick in a half dozen hard thrusts before he cums with a series grunts and groans as he fills your pussy, spilling thick and warm until you feel his seed leaking over your ass. 

“Fuck,” he groans, collapsing on top of you. 

You wrap yourself around him, holding him tight while he’s still inside you. The first time he tries to pull away you don’t let him so he settles between your hips and you kiss and touch each other until you finally release him. 

Rolling off you he lies on his back, breath quick with one hand on his chest. 

Everything is sticky, not just the mess between your legs but every inch of your skin is covered in sweat, most of it his. It feels claustrophobic, a rising crescendo emerging from somewhere deep inside. It starts as panic in your gut but twists into something else, an overwhelming sadness. An instant snapshot of your own mortality. 

_You almost died. Other people did. You were this close. So close._

All you can think about is the vast nothingness of not existing. The concept of simply being snuffed out is overwhelming and terrifying. You want to think about Sam, this new stage of your complicated relationship. You’re desperate to focus on the man lying beside you, the person you’ve missed for months who’s just confessed his feelings for you. But all you see in front of your open eyes is the image of Brent with that gun.

An unexpected sob tears from your throat and you slap a hand over your mouth in surprise. Sam actually jumps, jerking up into a sitting position as you wail, suddenly in hysterics. The panic returns, tightening your chest as your vision blurs and you roll onto your side, curling into a ball. 

“Hey,’ his hand is hesitant, patting your hip. “What’s wrong?” 

“I don’t know,” you blubber, body shaking like a leaf. “I just feel...everything. I can’t breathe.”

“You’re in shock,” he speaks calmly from somewhere above you. He touches you with fleeting hands, out of practice with a gentle touch. “I should have taken you to the hospital. We can go-”

“No,” you sob, reaching out for him. “Just stay here with me. Don’t leave.”

You cling to him, burrowing into his neck as he lies back. His arm hesitating before wrapping around you. This is arguably the most intimate you’ve ever been with each other and it’s the truest test so far. You don’t need a doctor, you need something to ground you, make you feel safe. 

And right on cue Sam fills the need as if you’d told him what to do. 

“I won’t let anything happen to you,” he whispers, a big hand stroking up and down your back. “Everything is going to be fine.”

“People died,” you close your eyes, pressing your nose over his rough five o'clock shadow. “I almost died.”

“But you didn’t.” He reaches down, pulling the blanket up over you both. “And you’re not going to, not for a long time.”

“Are you sure you want this?” You ask softly, fingers curling into the sparse hair of his chest. “All I can think is that you’re going to walk away again.”

“I won't,” he breathes, both arms tightening around you. “Try not to worry about that now. There’s going to be plenty of time for us to talk about this. Just close your eyes and try to sleep. I’ll be here when you wake up.”

You stare across the room at the open door of his closet, listening to his heartbeat. 

“Everything is going to be different now,” you whisper.

“I know,” he murmurs, already on the verge of sleep. “That’s how we move forward.” 


	18. Part Eighteen

Sam has always had a tendency to fixate on things.

As a kid, it was easier to hide. His teachers called him “special,” sometimes “gifted.” But really it was an all-consuming voracity to understand everything on any given topic.

When he was in sixth grade one of his teachers assigned him a report on ancient Greece. It was supposed to be a two-pager, easy peasy, something Sam could do in his sleep, but he got an  _F_ because he never handed it in. Not that it mattered. Two weeks later they were back on the road. He spent a month in the back of the Impala, reading by flashlight. He checked out copies of The Iliad and The Histories of Herodotus, only to drop them off at the next town’s library and pick up a copy of The Republic. By the time he was done, when he finally felt he had a grasp on the inner workings of the culture and the people of Greece, it was nearly a year later and the paper was long forgotten.

He knew he wanted to go to college and he knew where: Stanford. His future was in California and he could feel it. He had a plan. All he needed was to get good enough grades, he could fake the rest. The morning he left the motel where his dad and brother were sleeping, he honestly thought he’d never see them again. The guilt was real as he walked down the road, sticking out his thumb to every car that passed. It was an uneasy feeling that took residence in his gut and stayed there a long time.

That feeling lingered all through freshman orientation and well into his first semester. But then he met Jess and he found a new thing to put all his focus on. His family was fucked, he knew that without a doubt. But she was his chance to be normal, to be happy. No more monsters hiding in the dark; no more made up stories about the big bad to justify all the crazy his dad spouted day in and day out. No, Jess was all the good stuff in life. She was gentle and thoughtful and way too sexy to be with tall, skinny Sam. But inexplicably she loved him and he felt like he’d won the lottery every day.

Jess became the focus which seemed to help with his studies. She was everything and school was second which made things manageable for him. Against all logic, his girlfriend didn’t distract him, she allowed his brain to focus a normal amount, to move on instead of getting stuck on the details and needing days of research to answer every niggling question. Jess balanced Sam and he never took her for granted. 

When she died Sam thought he might die too. He’d never been in love before. Yeah, his dad and Dean were family and they loved him the way you love the people you also hate. But with Jess he’d been in love, ready to create his own family, to fulfill what he truly wanted in life, a normal job and a person to hold at night. Just when he finally believed the universe wasn’t so shitty, fate stepped in.

Dean came begging for him to join him on one last trip. Dad was MIA and Sam was powerless to say no. Dean needed their father in a way Sam never had. It was just a couple of days, he’d be back before anyone missed him and life would move on.

The police have maintained since the beginning that Dean killed Jess. They theorized that he stabbed her and then set the apartment on fire to cover up the evidence. For years Sam was so angry he let himself believe it. The anger would bubble up from his stomach, get caught in his throat and he’d think about how much he wished he could kill Dean.

So Sam did what Sam did best: he focused. After moving to the east coast he threw himself into law school. He lost himself in books and cases and facts. Anything but people.

Dean found him a couple of years later, showed up right after Sam graduated from Harvard Law. His brother told him how proud he was of his geeky little bro and that dad would have come but you know how he is.  

“Shouldn’t you be drunk or something?” Dean chirped good naturedly as Sam stared at him in the living room of his studio loft. “Celebrating with the rest of the class? Havard fucking Law School, goddamn Sammy.”

“Don’t call me Sammy,” Sam snapped back, folding his arms over his chest. He used to feel so much but as he stared at Dean all he felt was empty. “Why are you here?”

“Because,” Dean tilted his head, looking at Sam as if his brother should have already understood. “This is a pretty big deal. I’m proud of you.”

Sam stared at him in silence, both of them flinching as a car backfired outside.

“Did you do it?” Sam asked the question he’d wanted to ask for a long time. It didn’t hurt to think about her anymore. Jess was just a concept now, an idea of what could be taken away if you let yourself care. It happened to his father, his mother died and his dad went batshit crazy. Sam understood now, letting people in was just setting yourself up for pain and misery. It wasn’t worth it.

“Are you really asking me if I killed your girlfriend?” Dean laughed, smile fading as he realized Sam was serious. This tall, beefed-up version of his brother wasn’t the wide-eyed, big-hearted kid he grew up with. “No, I didn’t kill her.”

“Good,” Sam nodded. “Was it dad?”

“Jesus Christ,” Dean had had enough. “You think he’d do that? Why?”

“To prove a point. To get me to come back.” Sam dropped his backpack onto the table. “You should go, I have a lot of work to do.”

“You graduated three hours ago.” Dean watched Sam, realizing the extent of the damage. This Sam wasn’t his Sam at all, not anymore. “You got work to do?”

“I have to find a job, Dean. I have goals.” Sam waved his head. “Please don’t come back. This can be goodbye.”

“You mean that?” Dean asked, lips pursed trying to suss out if this was an act, but it wasn’t.

“Fuck, Dean,” Sam turned, arms spread wide with desperation. “Just leave me alone. I want you and dad to stay out of my life.”

“I hear ya,” Dean looked at Sam one final time before walking out.

In hindsight Sam’s not sure what he believes truly happened all those years ago. His dad might have killed Jess, maybe to teach Sam a lesson about family and leaving. Maybe he was delusional, maybe he thought she was one of his demons. Who knows. Maybe it was Dean after all, the old man did a real number on his brother. Dean was, and is, a true believer, he always has been.

From that moment, Sam worked. He put in eighty-hour weeks, he took chances and he built an empire. With success, isolation came hand in hand. The more money and power he gained the more he saw the worst in people. Everyone wanted something from him. It was easy to become the infamous Sam Winchester he is today.

And then you walked into his hotel room.

He’s always been able to read people, a talent that’s served him well through the years. So when you looked at him that first time, pupils widening, that nervous swallow you still get when you’re excited, he knew you saw him.

For most people, the initial attraction to him is the celebrity of his success. He’s in an elite group of powerful men recognizable by the general public, which has always made him uncomfortable. Strangers in the street do a double-take, trying to figure out how they know him. Sometimes he can hear the whispers as a wife leans toward her husband.

_“Tim Cook? No, but he’s someone, I know I’ve seen him before!”_

But when you reacted to him, and he saw that pulse of excitement in you, there was nothing else but raw attraction that you didn’t even understand yourself. You didn’t want him, or his attention, in fact, you would have faded quietly into the background if he’d have let you. Something about that appealed to him.

For a long time, it was just sex. He meant what he said. He had needs and you were beautiful with that tight little ass. And to top it off you got wet every time he so much as raised his voice. It was just sex and then one day it wasn’t. It was something more, a small, excited feeling that he hated and denied.

There were two others before you. One woman he paid, the other wanted more from him. Neither of them sparked anything inside him.

But you did.

You asked questions, personal things that no one had dared ask in a long time. You touched him, held him after you came like you already knew he cared for you. The way you rested your head on his shoulder and your arms wrapped around him, dug up old feelings.

Sam hated those feelings with a passion. He still does.

Part of him wishes he’d never confessed them to you. He should have saved you from Brent and sent you on your way.

He’s not good for anyone, he’s a slow working poison. His cold, dead heart will leak its toxin like arsenic until one day you’ll be just as numb as he is. He’ll break you. And you’ll hate him for it, that much he knows for certain.

-

“She’s been like that for hours,” Sam explains, pacing back and forth in front of the bedroom door. “She can’t get warm.”

You woke up like this, shivering uncontrollably.

“Look at me,” the doctor shines a light in one eye, then the other. “Are you having any auditory symptoms? Sounds that shouldn’t be there?”

“There’s, um,” you pause, closing your eyes and honing in on the sound. “A ringing. It’s distant but constant. It started a few hours ago.”

“Take a deep breath,” he instructs, placing a gentle hand on your shoulder. “What you’re feeling is normal. Everyone reacts differently and after what you went through it would be strange if you weren’t experiencing any repercussions.”

“What do we do?” Sam moves to stand behind him, crossing his arms over his chest as he stares down at you. If you didn’t know better you’d think he was pissed.

“Well, I can prescribe something for the panic attacks, but what she really needs is a support system and time. She should see a therapist and it should happen soon. Tomorrow at the latest. It’s vital to involve a professional as soon as possible. Will you be staying with her?”

“Yes,” Sam nods, his eyes shifting from you to the doctor.

“Good,” he turns back to you. “You may start to feel more acute feelings of loneliness and isolation. It’s normal, but you shouldn’t give in to those tendencies. You need to talk, to be around people. And I meant what I said, seek professional psychiatric help. It doesn’t make you strong to try and handle this on your own. It only makes you foolish.”

-

Sam settles next to you on the couch as a half dozen men and women mill around his living room. A tech sets up audio recording while another focuses a video camera on the two of you.

“I’m agent Ashburn with Alcohol, Tobacco and Firearms. This is Agent Murtaugh with the FBI. We’re a joint task force and we want to make this as easy as possible. Hopefully, we won’t need to speak with you a second time.” She offers a practiced smile, shifting her gaze to Sam. “We’ll probably need you for follow up. More than one I’d guess.”

“I understand,” Sam nods, crossing one leg over his knee, his arm extending over the back of the couch behind your head. “Do you know how many people were injured?”

“As of right now we’re looking at nineteen injuries and seven fatalities.” Murtaugh leans forward, both arms resting on his knees. “It would have been a lot worse if you hadn’t gotten to him.”

You shift in your seat, looking down at your hands. You want to ask about Max and Tim, but at the same time, you’re afraid of the answer.

“Did you see a doctor, Y/N? We have a lot of resources available.” Ashburn reaches out, tapping the coffee table gently.

“Yeah,” you look at her, feeling your heart speed up. You’ve been fighting these random panic attacks all morning and the medication only helps a little.

“We had someone come over this morning,” Sam elaborates, a hand squeezing your shoulder. “She’ll be fine.”

“Just to clarify,” Murtaugh gestures with the end of his pen between you and Sam. “What exactly is the nature of your relationship?”

That question is so complicated you don’t even know how to begin thinking about an answer but Sam picks up the slack without skipping a beat.

“Romantic,” Sam states simply.

“Right, okay.” Agent Ashburn scans through her notes, looking up to Sam. “We’re allowing you to stay with her, but these questions are for Y/N. I need her to answer, no interruptions.”

“I understand,” Sam confirms and you close your eyes for a moment, trying to focus.

“Prior to him being let go, did Brent ever say or do anything that you found odd or aggressive?”

“No, he was nice. A lot of the junior associates are assholes, sorry,  _jerks_ , but we all liked Brent.” You think back scanning your interactions with him. It’s all true, he seemed like one of the good ones.

“Would you say you were friends?”

“No. I mean, he was a work friend, but we’re not close. I said “hi” to him every morning for six months. We talked a couple of times a week. He was more than an acquaintance, less than a friend.” You look from the agents to Sam. You want to give them the right answer, to help. “I’m sorry, I’m trying, I just-”

“You’re doing great,” Sam gives you another squeeze, his voice more gentle and encouraging than you’ve ever heard him before. It’s almost unsettling.

“Yes, you are,” Murtaugh jumps in. “You’re doing what helps us most. Just talk, don’t overthink the answer. Sometimes we get the details we need when people don’t even realize it.”

“Okay.”

“Did you ever spend any time with him outside of work.”

“A few times,” you shrug. “On Wednesdays everyone goes to the bar, he went a few times. I never really talked to him though.”

“How about after he was fired? Did you have any contact?”

“Yes, I texted him. I can show you if you want.” You reach for your cell phone and Sam picks it up from the side table and hands it to you. Pulling up the text you read it out loud. “It was the only time I ever texted him. I just said  _We’re all so sorry about what happened. Hope you still show up for drinks._ ”

“He never responded?”

“No,” you hand Ashburn your phone and she reads it.

“We’ll need to keep this,” she explains, handing it off to a tech who drops it into a plastic bag. You shift towards Sam, looking down at your hands. “Is something wrong?”

“It’s just, ummm, Sam and I text sometimes. There are private messages…photos.” You can feel the heat in your cheeks.

“Well, I won’t lie. Our techs will comb through everything but we’re only interested in your correspondence with Brent.”

“God,” you sigh, trying to remain calm. You should have deleted the thread between you and Keith Campbell, some of the things on there would make Ron Jeremy blush.

“Don’t worry, they’ve seen it all.” Ashburn winks, trying to keep things light-hearted and you want to sink into the couch. “I have to ask. We’re unclear on Brent’s plan. We’re not sure if he was targeting specific people, or if it was random. We know he was upset with Sam, do you feel that he may have focused on you because of your relationship with Sam?”

“No,” you sigh, the very thought is unnerving. “No one knows about us.”

“I see.” Both agents ask question after question, right down to the mundane details of your breakfast that morning, and then they go through them again. It’s almost three by the time they’re done with you. Retreating into the bedroom you turn on the TV while Sam begins his interview. You doubt you gave them anything, any insight, but Sam might. You don’t know the details of his termination, it’s possible he holds all the answers.


	19. Nineteen

Sam’s lying on his back staring at the ceiling. One hand is spread over his chest, strumming his fingers, lost in his own mind. Is he nervous? Perhaps he’s uncomfortable having you here, now that the two of you are this undefined thing. You’ve been in his bed countless times but you can recognize this feels different.

“I feel like you’ve got something you need to say,” you throw out there, wondering if he’ll even respond. In the past when you asked a question he didn’t like, he just ignored you.

“I don’t like labels,” he answers without skipping a beat.

_There it is._  Sam is just a guy, after all. A guy worried about labels and expectations. This must be killing him.

“I know,” you sigh.

“It’s ridiculous.” He’s disgusted.  “Are you my girlfriend? Are we in middle school?”

“You hate being like anyone else, don’t you?”

“Yes,” he retorts immediately, then lays there as a million silent thoughts swirl between you.

“So, we don’t define ourselves. Not right now, anyway. I don’t need a title to be with you.”

“Good,” he nods. “Neither do I.”

“But there are things that I do need,” you continue, feeling him suck the air right out of the room. “I need commitment. I need you to tear up that contract. I need you to push yourself, it’s gonna be uncomfortable.”

“I’m well aware.” His voice is even, resigned. He already knows all this but it still had to be said. After all, Sam always lays out clear expectations for you, so you figure he deserves them in return. Shifting gears he looks at you, reaching over to grab your wrist. “How do you feel this morning?”

“Better,” you explain. “A lot better than yesterday, not too overwhelmed.”

“I’m glad. I was worried about you,” he confesses easily.

_He was worried._  He cares. The thought is still a novelty.

“There’s work I need to do. I have conference calls all morning and all the senior staff are meeting downtown after lunch. This is going to be a mess, I can’t expect anyone to work in a building where people were murdered, we’ve got to figure an alternative workspace.” It’s not that he’s callous, well, yes he is, but he’s also running a billion dollar business. Shooting or no shooting he’s the person who makes sure all the balls stay in the air. “Will you be alright going to the doctor on your own?”

“Of course. I’m not falling apart, I’ll be fine.” That part is true, right now you’re don’t feel much of anything.

“My schedule will balloon as the week goes on. If you need me you’re going to have to tell me so Pepper can rearrange my schedule.”

The office is closed for an undetermined amount of time but that doesn’t mean there aren’t legions of employees working from home, keeping the campfires burning while the situation evolves.

“It’s alright, really. I’ve actually got a lot I need to figure out. I was supposed to leave for Chicago. I sold all my furniture, gave up my apartment. I donated most of my clothes to Goodwill. I’ll stay busy.”

You watch him grimace, a look of pure displeasure pulling the corners of his mouth down. He takes a breath and clears his throat.

“You can stay here, with me,” he offers, looking at the ceiling fan.

“That’s not a good idea and we both know it. I’m here a lot as it is. Besides, you don’t really want me to move in.”

“No, I don’t,” he confirms, watching for your reaction. “It’s not you, I want you, I-”

“We both need our space, Sam.” You let him off the hook. “I don’t expect you to leap from weekend sex partner to a white picket fence. I get it.”

This seems to relax him a little, his face going slack and then another thought comes to him, this offer less laden with dread.

“You can stay at my place in the city. I’m only there a couple of nights a week.” He looks proud of his compromise and you hate to disappoint him but this isn’t what you want either.

“A couple of nights a week and the weekends is damn near close to living together. I want to get to know you organically. If this is forced I don’t think we’ll even have a fighting chance.”

“We don’t know each other?” he counters.

“No, we don’t.”

“What do you mean? We know each other.”

“Sam, you probably know me more than I know you, but we don’t really know each other at all outside of how to give each other an orgasm. We’ve got a lot to learn about each other.”

“Okay,” he looks like you’ve just given him a month to live.

“Why does that make you so uncomfortable?”

“I’m not sure there’s much to know.” He shrugs.

“Sure there is. Under all that well-manicured exterior you’ve got a lot going on, there’s a human being. I’ve seen him from time to time. That’s the guy I want to know more of. I want your past and your future. I get that’s going to be hard for you.”

“You might not like what you find.”

“Stop doing that. You always talk like I don’t know what I’m getting myself into. I know the very idea of opening up makes your skin crawl. But you’re gonna have to try. We both are.”

“Is this the start of you telling me what to do?” There’s a sly little smile, a hint of levity.

“Well,” you grin. “I can’t be submissive all the time. Sex is one thing but I’m a complicated person. I’m not always going to do what you tell me. That part of our dynamic has its place, but I need to be able to speak my mind. I’m one of the few people who’s going to tell you no.”

“I have no doubt.” Sam nods, clearly in his own thoughts.

You lie there a while longer, still struggling with the art of organic conversation.

“Your dad taught you how to do crazy stuff, huh?” you ask quietly.

He side-eyes you, taking a breath. “A lot of stuff I wish I could forget.”

“You saved lives, that has to be worth something.”

“I suppose.” He tilts his head back into the pillow. “It’s a miracle anything good could come out of the mess he made of our lives. I am the way I am because of him. Dean and I both suffered, we just dealt with it in different ways. In another life, you’d see my face on the five o’clock news too.”

“Why was your dad like that?” you whisper.

“My mother died. It was a house fire but dad couldn’t let it go. He couldn’t accept that the person he loved most was killed by faulty wiring. He needed to believe that it was bigger than that, some looming evil. Over the years he convinced himself, and my brother, that monsters existed.”

“Monsters, like…evil people?”

“No,” he snorts, turning his head to look at you. “Monsters like ghosts and demons. He brainwashed himself and then my brother. Even as a kid I knew something wasn’t right. The stories he’d tell. He pulled Dean out of school. We lived out of a car and motel rooms until I finally had enough and left to go to college.”

“I’m sorry,” you’re not sure what else to say.

“Don’t be.” Sam gives your arm a soft squeeze. “I need to get up, I’ll see you tonight.”

The day is filled with menial tasks that help distract from the weight of real life. You go to Macy’s in an attempt to flesh out your wardrobe and scout out a couple small apartments for rent. After lunch is your first appointment with a female therapist that you end up liking. It’s just the first session and you don’t really get into anything but you like her. There’s something about her that reminds you vaguely of your grandmother and you’re already looking forward to going back.

-

It’s almost midnight when Sam comes home, wandering into the kitchen where you’re eating peanut butter toast over the sink.

“Hello,” he looks at you, setting his briefcase on the counter.

“Hello,” you return, staring at the veins in the back of his hands as he sets a stack of mail on the counter. “Did you have a good day?”

“I don’t know about good,” he huffs, shrugging off his suit jacket. “It was productive.”

He looks at you, holding something back and then moves toward the pantry.

“Sam, can I ask you something?”

“Of course,” he plucks a seltzer from the refrigerator and cracks it open.

“You haven’t touched me. I’ve been in your house, in your bed and you haven’t really touched me, not like you used to.”

“That’s not a question,” he volleys back, setting the bottle on the countertop.

“I guess it isn’t.”

“I didn’t know if that was something you’d want…or you’re ready for.”

“I’m not broken,” you inform him, slinking closer. “I’m ready.”

“I don’t have to be so…demanding. We can start slow and-”

“No.” You stare at him, both hands on the counter. “What happened, the shooting, made me feel like there was so much that’s out of my control. And there is. But when we’re together you’re in control and I trust you completely. I need you to be in control of me.”

He blinks, that familiar hungry look spreading from his eyes to his mouth. He shifts into a role that’s clearly much more comfortable for him, his hand palming the crotch of his pants.

“Take your clothes off.” It’s a straight forward, uncomplicated command that carries so much weight behind it. Those words are how he’s started almost every encounter from the beginning and it feels like a lifetime since last he said them.

You strip, shimmying out of your jeans, and pulling the tank top over your head. Your bra comes off next, leaving only cotton panties that you put on out of habit. He looks from your covered pussy back to your eyes, saying nothing. You leave them on and pull at your ponytail, letting your hair fall around your shoulders.

“I told you not to wear those.” He blinks, taking one step forward.

“I didn’t listen,” you look up at him, biting your lip. “I did a lot of things during the last couple of months. I used my vibrator, I put it inside me. I came without your fingers or your cock in my pussy. I’ve broken a lot of rules.”

Half of that is a lie. But it doesn’t matter, you want him to discipline you. You want his hands on you hard and dirty and rough. The punishment is always your favorite and you’ve craved it like you’ve craved his scent on your skin after he fucks you.

After everything that’s happened you want the intimacy of this sexual connection, boundaries, and limits he knows how to push, even when you don’t.

His eyes set, locking on your face with an expression that might be anger? Arousal? With him, it’s hard to tell, but it’s the exact reaction you were looking for. With two steps he’s got one hand in your hair, twisting until you’re on your tiptoes.

“Living room,” he growls, walking behind you, guiding you out into the main living area and toward the couch. After a final yank, he releases your hair, pushing you forward over the arm of the couch. “Bend over.”

You comply, quaking with excitement as you place open palms on the cushion, sticking your ass out.

“You need a reminder,” he explains. There’s a rustle of clothes, you know the sound well. You stay in place, prone and exposed as he rolls up one sleeve, then the other. After a moment his hands are on your ass, kneading your cheeks through the cotton. His thumb presses forward, wedging the material into your pussy. You’re already wet, the panties sticky with arousal as he confirms your excitement. “No panties was the first expectation I set for you. Did you forget?”

“No, I didn’t forget,” you confess, waiting for the reaction. But there is none, he doesn’t say a word as he hooks his fingers into the elastic and drags your panties down until they’re around your thighs.

_Crack._

The first snap of his hand comes down on your ass with a speed and force that knocks the air right out of your lungs. You yelp, face dropping into the cushion as a throbbing sting bursts to life. He’s not playing around.

“What do you say?” he asks, standing tall behind you, hands on his hips.

You know what he wants, the usual thank you that gets him off. But you have other plans.

“I don’t think I’ve learned my lesson,” you pant, getting back up onto your hands, assuming the position.

He grunts, taking a moment to look at your backside before inflicting the next set.

_Crack._

_Crack._

_Fuck._  Tears spring from your eyes as you blink wide trying to control your response.  This is right at the edge of your well-defined limit. These are the unyielding blows he’s only used twice before.

_Crack._

_Crack._

The next two are just as bad. You’re glad he can’t see your face because the tears would stop him. This isn’t the normal trickle from the corner of your eyes, this fucking hurts, these are tears of pain but there’s also something else underneath. The agony making the ache between your legs grow and pulse.

You want more.

“What do you say?” he asks again, a hand resting on your lower back as his thumb strokes back and forth.

“Harder.” The request comes as a plea, a desperate sound as you wiggle your ass back toward him. “Please,  _harder_.”

There’s nothing and then he’s moving to the side, one hand pressing his weight into the base of your spine to keep you in place. His free hand is working at something and in a second your suspicions are confirmed when you hear his belt slip from its loops.

“Tell me what this is for?” he asks, the sound of leather on metal making you hyper-aware.

“I disobeyed,” you whisper, pressing your face into the couch. “I’m sorry, I need you to teach me a lesson.”

Then he gives you exactly what you need and you tip off the edge of that former limit and freefall into a new abyss of pleasure and pain.

_Crack._

_Crack._

_Crack._

_Crack._

The leather of his belt bites into the tender skin of your ass with sickening precision. You cry out, flinching as each stroke crosses over the previous, the pain bordering on unbearable. While it hurts it’s also incredible. You feel more alive than you have in a long time, squirming under his unrelenting hand.

Your clit is throbbing, pussy clenching and nipples hard as pebbles. In this kind of heightened state of arousal, you want all the vicious, wild fantasies that normally only cross your mind right before you cum. He could do anything he wanted to you when you’re like this and you’d get off on it.

You’re not sure if you can take it, but you still ask again. Your fists clench into a ball, fingernails digging into your palms.

“Harder,” you beg.

_Crack._

_Crack._

The lick of the belt strikes twice more and you rock forward, feet kicking as you suck in a breath.

“Thank you,” wheezing you turn your face to the side to take a full breath, feeling your backside thump with each beat of your heart, now racing in your chest. “Thank you.”

His fingertips ghost across your ass as he admires his handiwork. He’s never left a mark on you before, at least not from a spanking, but this will. You can already feel it.

“Get on your knees,” he instructs, his hand on your arms to help you up. When he sees your face he stops for a fleeting moment, wiping away tears before helping you sink down onto the carpet. “Open your mouth.”

You look up at him, bracing both hands on his thighs and taking his cock into your mouth.

“Right down your throat, take it all,” Sam orders, two hands curling into your hair to keep his shaft deep. It’s been a while and you gag at first, finally relaxing your throat and letting him begin to fuck you slow and rooted. He makes strained sounds, grunts, and groans only loud enough for you to hear.

There’s only the sound of his enjoyment and the wet, squelch of him fucking your mouth. Spit drips down your chin, eyes watering as you fight to take him deeper and deeper until his balls are rocking into your chin with every stroke.  

You’re sitting on your heels and you can feel the aftermath of his belt as you suck his cock with enthusiasm. You probably won’t be able to sit tomorrow, but it’s worth it. No one else can make you feel like this. There’s a freedom in submission, letting someone else take total control and releasing that part of your mind. There’s no thought, no outside desires, just this moment and the way your body responds to every touch and stroke.

His hips speed up and you feel him getting close. You prepare for the taste of him on your tongue but instead, he pulls out, leaving you a panting, drooling mess looking up for instruction.

“I’m not even close to done with you,” he snaps, fisting his wet cock from base to tip. “Get up and get yourself into the bedroom.”

-

Your hands are tied behind your back, fastened securely with that notorious belt at the base of your spine. One of his ties is wrapped around your eyes, and your own white panties are balled up and shoved in your mouth as a gag.

You’ve been sitting in his lap for the better part of an hour with his thick, hard cock deep in your cunt. He hasn’t let you move, just sitting with a slick pussy stretched around his girth as he plays with your tits.

Your right nipple is on fire. He’s been taking turns sucking on them, but your right has become his favorite as his teeth sink into the swollen flesh, drawing a muffled groan from your lips. Your other nipple is caught between his thumb and forefinger, pinching hard and tugging until you think you can’t take anymore.

And your ass is on fire, those lashes left pain that springs to life as the hair of his thighs scratches over your buttocks.

You’re so fucking wet you can feel the slippery slide of your thighs over his, your arousal leaking from around his cock as you squirm, muscles tightening around his length. If he even gets near your clit you’ll cum. There’ll be no asking for permission, you’re desperate and right on the edge of slipping into ultimate pleasure as his mouth pops off your nipple, and his fingers close around the wet peak.

He’s got both nipples between his fingers now, pinching hard and twisting slowly, back and forth as you groan and sweat on top of him.

Sam’s taking his time.

“I’m going to cum on your tits,” he promises, voice low he pulls both nipples upward until they’re painfully taught. “Or maybe your face…would you like that? Make you get on your knees with your hands tied behind your back and cum all over this pretty face…let you have a little to swallow.”  

“ _Ahmm_ ,” you nod yes, hissing as he works your tits. Before Sam, you never really had the desire to have man a blow his load on you, but right now you’d beg him to cover you in his spunk.

“Do you want to cum?” He asks softly, swapping back to suck on a sore and aching nipple.

“ _Heeze!_ ” You garble enthusiastically.

Reaching up he pulls the panties out of your mouth, letting you take a normal breath.

“Ask me for it,” he commands, slapping your breast lightly.

You wiggle and groan with his cock stuffed deep, more eager to please him than he could probably imagine.

“Please let me cum, Sam, please.” You’re not ashamed to beg, grinding your hips downward, beginning to rock back and forth. “I wanna cum and I want you to cum all over me. Please, I wanna taste you so bad.  _Please. Please._ ”

“Fuck,” he grunts, lifting you off his cock with a flex of muscle. He hoists you easily over the side of the bed and deposits you onto the floor, reaching down to take your makeshift blindfold off.

You gaze up at him expectantly, sticking your tongue out as he thrusts his cock in your face and strokes himself. Moving closer he wedges a foot between your thighs, letting your clit rub against his shin bone.

“Make yourself cum,” he offers mercifully.

That wonderful combination of humiliation and desperation sets in as you urgently rub your cunt up and down his leg, leaving him wet with your slick. In no time you cum, jerking and moaning with your mouth open as your pussy clenches painfully around nothing. It’s an immense relief after all this time, humming and vibrating from head to toe.

Sam jerks himself faster until he’s spurting all over your face, coating you in hot ropes of seed, making sure to get some in your mouth. You’re still cumming as you swallow his spunk.  He lets the head of his dick tap your cheek, then slides between your lips for a gentle suck as he comes down from his own peak.

“Shit,” he sighs, finally pulling his cock from your mouth. “Here,” he drops down to his knees, releasing your hands then thumbing cum off your cheek. “I forgot how perfect you are.”

-

“We need a safeword,” Sam suggests, stepping into the shower behind you.

“Why?” you ask, looking back at him. “I guess I always thought our safe word was stop.”

“That’s fine, it can be, but we’ve never talked about it. I never thought we needed to be that…structured,” he explains, stepping under the spray.

“But we need one now?”

“We need one when you want me to leave those kinds of marks on you.” He nods toward your ass and you twist around trying to get a look at yourself.

“I don’t know what got into me, I just wanted it.” You blush, offering a small smile. “Too far?”

“No,” he shakes his head, slicking hair back with two hands. “I told you, as long as you’re getting pleasure from it, then I am too. But if we’re going to venture into a territory where you end up with bruises like that, I need to be one hundred percent sure that you want it. It would be easy for me to really hurt you, and I have no desire for that.”

“Okay,” you agree, looking him over from head to toe. You hope your new status, whatever that might be, will allow you this view more often. Sam is a beautiful man, long and lean and strong. He’s something to be admired and you’re the woman for the task. “Well, our safe word should be ‘stop’ then. No confusion.”

“Agreed,” he looks at you, water dripping from his hair and pulls you close, lowering his mouth down for a kiss that still feels forbidden. His lips are so soft compared to everything you just did, a sweet kiss that’s the cherry on top of a truly satisfying evening. When he pulls back he stays close, eyes sweeping over your face. “You should stay here with me until you find an apartment. I work so much you’ll have the place to yourself most of the time. I would like it if you stayed.”

“Then I’ll stay,” you confirm, leaning into him. “Just until I find something.”

-

 

Parts 20, 21 & 22 are currently available on [Patreon](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) for a monthly pledge of $2.50. This includes early access to all my stories and Patreon exclusive content.  >> [CLICK HERE](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.patreon.com%2FCleverDame&t=NmVmNTc1Y2VjMmJhZjhhY2NiMTgyZWQ0OWJlMDJkOGNlODNjOTZiYyxmZThhTUJPRg%3D%3D&b=t%3A0mHNq87vSfIQ59G3elMpDw&p=https%3A%2F%2Fthecleverdame.tumblr.com%2Fpost%2F182597234598%2Fthe-woodsman&m=1) <<


	20. Twenty

“Holy shit,” you mutter, staring at your black and blue ass in the mirror. These marks aren’t faint or small. Your backside is covered with thick, deep blue welts from his belt. You woke up on your stomach, only to wince in pain once you rolled over. Then you sat up and nearly yelped at the ache. But now as you stand naked in the bathroom you can’t help but smile, twisting around to get a better look. While you’re going to have a hard time sitting down, it’s a thrilling reminder of last night. A reminder of something new and this connection that’s growing between you and Sam. 

Your phone rings and you glance at the number, sighing before answering. 

“Hey, mom-”

“Don’t you ‘hey mom’ me. You said you’d call me back and I haven’t heard a peep in forty-eight hours. I’ve been calling and calling.”

“The FBI took my phone. This one came by courier this morning, honestly, I just turned it on like ten minutes ago.”

“Are you trying to give me a heart attack?” 

“Of course not,” you roll your eyes, glancing at your butt one last time. “A lot’s happened in the last twenty-four hours.” 

“Do you want to come home? You can move home with your dad and I. We haven't touched your room.” 

“I’m not moving back to Albuquerque. I’m okay, really.”

“And what? You’re headed to Chicago all by your lonesome after what happened? That’s not a good idea.”  

“No, I’m staying here in Boston. Things have changed.” 

“I’ll come there, then. I was looking at flights this morning. Your father and I can be there by this afternoon.” 

“Mom, seriously, I’m fine,” you suppress the urge to get riled up. She loves you, but sometimes it’s too much. Slipping into the closet you find your tiny section of clothes amid Sam’s vast wardrobe.  

“Don’t be ridiculous, of course you’re not fine,” she fires back. “Who would be alright after something like that? I’m coming there to take care of you.”

“No, mom, just stop and listen to me. I’m a little shook but honestly, I’m doing good. I’m seeing a therapist. I’m going to be late for my appointment if I don’t hurry up and get dressed.”  

“No one should have to go through this alone, sweetheart.”

“I told you, I’m not alone.” You stop to look at the empty bed, Sam was up and out the door before the sun came up. “I’ve got people here. Just please, stop worrying about me so much. I’ll call every day, I promise.” 

“I don’t like this. You said you were moving because there was nothing left for you in that God awful city and now you’re staying?” 

“Things just... _changed._ I’ve got positive things here, but it’s hard to talk about it. I feel like shit for talking about anything good that’s in my life when people were just killed. I need time to process everything.”

“Who’s going to make sure you eat? Your appetite is always the first thing to go when you’re stressed. Are you in a hotel? Where are you staying?”

“I’m with a friend until I get my living situation figured out.”

“Thank God, hotels are so impersonal. With those tiny soaps and the coffee is never good. You need a home.” 

“Look, I have to go. I’m going to call you later, okay?”

“Alright, I love you so much.”

“I love you too.” 

As you hang up you walk to the small dresser at the back of the closet and open the top drawer. The two photos that used to be on display are now tucked out of sight You take out the one of him in college. He’s so happy and in love, it’s hard to imagine your Sam is this same person. 

If nothing else it’s a reminder of the fact that people are capable of great change.

-

Walking down the hallways of the hospital you glance down at the paper in your hand with a room number written on it. Pausing at room 7059 you confirm the name scribbled on the dry erase board and knock. 

“Come in,” calls out a male voice.

“Hi.” You shuffle inside, leaning around the curtains pulled in a half-circle around his bed. “I’m sorry if I’m bothering you.”

“You’re the last face I expected to see,” Tim laughs and then coughs, grimacing in pain. “But you’re not bothering me. I’m bored out of my mind.” 

“Are you sure? I can come back later…” you’re already backing out of the room as he leans forward, wincing in pain. 

“Please, just sit down. I’d like the company.” 

You step around his bed, sitting in the plastic chair pulled up beside it. Your eyes flutter closed as your ass throbs. 

“Oh, I brought you something,” you remember, reaching into your bag and pulling out a copy of The Reckoning by John Grisham. “It was this or Danielle Steel. The gift shop didn’t have a lot of options. I don’t even know if you like to read.” It’s at that moment you spot a Kindle lying beside him on the bed. “Or if you already have an e-reader with access to any book you want.” 

“This thing is my mom’s, it’s full of Agatha Christie novels and I don’t have her password to buy anything else.” He holds up the Kindle. “I _do_ like to read and I prefer books. Thank you for bringing me something other than flowers.” 

He gestures around the room. 

“Wow,” you look at the dozen or so bouquets and potted plants. “I guess people go with what they know.”

“I guess,” he nods, smiling at you. “I’m glad you’re alright,”

“Thanks. I’m glad you’re alright too.” You shift in the chair. “That’s why I’m here. I don’t think I would be alive if it weren’t for you.”

“Eh,” he grumbles, looking away. “I’m not the hero in this story. Winchester is the one who took him out.”

“True, but you distracted him. People were running and you stepped forward, put your arms out in front of us.”

“That was nothing. Just instincts.”

You shrug. “Instincts that bought the rest of us a few seconds. Sam got there just in time, but if you hadn’t tried to help us, I don’t think it would have ended the same way for me. Thank you.”

“You’re very welcome.” He nods, clearing his throat. “I heard Callie, the redhead who did the corporate travel arrangements...she died this morning in surgery.”

“Yeah,” you confirm, feeling the sadness swell into your throat. “Max died last night. They thought he might make it, but he didn’t.”

The death toll kept rising. It turns out Brent used a particularly nasty bullet designed to do the maximum amount of damage.  A lot of the people who survived the initial attack are struggling with serious complications. 

“Shit.” Tim sits back against the pillow. You’re both silent as the murmur of the TV rambles in the background. “I’m starting to think I must be lucky. This is actually the third time I’ve taken a bullet. I’m three for three.”

“I heard that. You never know what’s rumor and what’s not but people said that’s why you left the service.” 

“That was the second time. But the better story is the first time. I was just a kid. My brother accidentally shot me with my dad’s .22. He was grounded for a year and I got all the chocolate ice cream I could eat. Hell, I still do. My mom brought me some this morning.” 

“Maybe you are lucky,” you laugh, checking your cell phone.  

Two messages are scrawled across the screen. 

_**Sam:** _ _Meet me for lunch._

_**Sam:** _ _Parish Cafe at 1:30_

“Someone important?” Tim grins. 

“Important and demanding,” you chuckle, responding _see you there_ and put the phone away. “Look I know I don’t know you and I don’t want to make this weird, but if you’re feeling up to it do you think we could get together next week?”

His eyebrows shoot up and you backtrack, shaking your head in embarrassment. 

“I didn’t mean...I...God, I’m bad at this. I’m seeing a therapist, and yesterday she suggested that I reach out and try to connect with some of the people who were there when it happened. I was kinda hoping Millie would join us, maybe Lexi - God bless her.”

Tim laughs out loud at that, nodding in agreement. 

“Sure, I didn’t have much of a social life before all this and I’m guessing I’ll be a captive audience for some time.”  

“Awesome.”

“I thought you were moving? Seems like this would be the perfect opportunity to get the fuck out of dodge.”

You stare at him, a million thoughts merging all at once. 

“Things changed.”

“Important and demanding things?” he questions and you can’t help the blush that creeps into your cheeks. 

“Yes,” you whisper, getting up. “So, I guess I’ll see you next week then.”

“Just let me know.” He gives you a little salute. 

-

Sam’s seated in the back of the dark little restaurant, reading on his iPad when you join him. 

“Sorry I’m late,” you slip into the chair across from him, biting your lip as the sting of the bruises take your breath away. “I don’t think my Uber driver has lived here very long.”

“I could have sent a car for you.” He finishes what he’s reading before looking up. A flicker moves from his eyes to his mouth, just a ghost of a smile. “I like that dress.”

You look down at the black and white gingham summer dress you bought yesterday. “Thanks, it’s new.”

“I don’t normally see you this casual.”

“I guess that’s true,” you grin at him. He looks handsome today. Sam always looks good, but there’s something about when he doesn’t wear a tie and lets the top buttons of his shirt lay open that you just love. “You like it huh?”

“Very much,” he confirms. He carefully places his tablet and his phone screen down on the table. It’s something new he’s started doing when he intends on giving you his full attention. 

“So,” you take the cloth napkin, folding it over your lap. “This was unexpected. I thought you’d be too busy.”

“Not for you,” he responds succinctly and you feel your heart speed up. 

This is Sam trying. 

“You keep saying things like that and we might need to get a room after lunch,” you laugh, then realize how much easier this feels, more natural than before. You worried it would be hard to relax around him, but that’s not the case. 

“That could be an interesting prospect,” he trails his finger around the edge of his water glass, lost somewhere between amusement and arousal. “Not today, but another time.”

“I’ll look forward to it then. You know, I haven’t officially asked yet, can I have my job back?”

“Of course,” he scoffs, “In fact, I’m thinking of placing you as a sort of mentor to a new guy I have coming in.”

“A mentor? I’m barely a secretary.”

“I meant more of a mentor for navigating the people, the office politics. What happened with Brent can’t happen again. I need someone down in the trenches watching the junior associates. After what happened with you and Max, and now Brent it’s clear it’s the wild west and I intend to reign it in. I should have seen it before.”

“What exactly happened...with Brent?”

“It’s not clear yet. I think Brent took the fall for a couple of other guys, they set him up to be a scapegoat. I suspected it at the time but I also have to walk a fine line. I can’t accuse senior staff of lying unless I have something to back it up. It undermines their authority. I’m bringing in several people from the outside for oversight, we need a fresh start.”

“What are you going to do about the building?”

“Have it demolished. I can’t expect anyone to work there. I was focused on expanding the campus, but now that’s futile. There are two buildings downtown, big enough for everyone but I have to ensure it’s the right fit. I’m headed there this afternoon if you’d like to join me.” 

“I’d like that,” you watch him pick up the menu. 

You could get used to this. 

 

**Two Weeks Later**

“You found a place?” Sam inquires, looking through the stack of mail.

“Yup, it’s a loft. It’s small but there are tall ceilings so it doesn’t feel claustrophobic. Lots of windows. It’s exactly what I need right now.” You grin, plopping down on his couch. “They said I can move in next Monday.”

“Are you ready for that?” he inquires nonchalantly, skimming over a letter. “You said your therapist suggested you shouldn’t be alone, not for a while.”

“I’m not gonna be alone. We start working at the office on Wednesday, I always spend weekends with you and I’m hoping maybe I could see you during the week sometimes...it’s been nice spending time together, you know, other than sex.”

You watch him absorb this confession, a thoughtful expression crossing his face as he sets the remaining mail aside and looks at you. 

“It’s been different than I thought. I haven’t shared personal space like this in a very long time. I assumed I would feel suffocated, but I haven’t. You’re easy to be around.” He delivers this information deadpan and your entire face goes hot. “It’s been nice.”

“Maybe you could come to my place sometime? I can try to cook something, and I’ll probably have a futon by then. Maybe even a loveseat if my boss gives me a raise with this fancy new position. You can see how the other half lives.”

“That sounds...terrible,” he grins, watching you carefully. 

“Yeah, it does,” you laugh out loud, genuinely happy for the first time in a long time. “But I am getting a new bed, I ordered it this morning. We could break it in…”

“You let me know once the futon arrives and I’ll drop by.” He gives in, checking his watch. “There is one thing we need to talk about.”

“That sounds vaguely ominous,” you chatter, giving him your full attention. 

“You asked me to void our contract. I had it taken care of this morning.” He gives a curt little nod. 

“I wanted to talk about that...about us and how this works now. I’d still prefer if our relationship remained private. For the time being at least.” You’ve been thinking about it more and more over the last few days. 

“I understand,” Sam agrees easily. 

“It’s just, people will assume a lot of things. And they’re nosey. I like this being just ours.”

“You don’t have to explain, I understand. My life entails more than you realize. No one pays attention to me because I don’t date actresses or get DUIs, but once you’re in the mix, eventually someone will take an interest.”

“We’re not very scandalous,” you snort, “Well, I guess kind of, but not in a ‘Page Six’ way.”

“True.” Sam looks relaxed, more at ease than you’ve seen him since this thing between you started. “You’re always welcome here,” he adds, before shifting his attention back to his work. 

-

“You start work tomorrow?” Carol, your psychiatrist, is always examining you. But that’s why you come here, to be an open book. You’ve always been open to the idea of therapy and after everything that’s happened this can’t hurt. 

“Yeah, going in on a Wednesday. We’re starting back up with a three day week.” It’s been a month since the shooting and life has inevitably moved despite the many changes. “I’m kinda nervous. I keep having this thought that I shouldn’t feel so normal. Like I’m waiting for the other shoe to drop and have some kind of a breakdown or something.”

“Are you still experiencing triggers?” 

“Yeah,” you admit. This is the most frustrating part for you. Ninety-nine percent of the time you’re fine but out of the blue you find yourself spiraling down this dark hole. The panic attacks hit you out of nowhere and disappear just as quickly. It’s normal, that’s what everyone keeps telling you, but the unpredictability of it is infuriating. “I went three days with nothing and then last night we were eating dinner and _bam_. I almost passed out. Five minutes later I was fine.”

“Was there anything that stood out about that moment? A loud noise? Someone yelling?”

“No,” you shrug. “I was in the kitchen. I don’t even turn the TV on anymore. I never noticed before how many guns there are. Someone’s always shooting or talking about it. The first couple of times it happened I thought that was it. CNN was on the background, maybe I heard something I didn’t realize. But I’ve officially marked that off as a possibility. The trigger must be something else.” 

“Well, just keep an eye on it. Next time it happens try to make a note of the details. Write it down right away, or take a video with your cell phone. We’ll figure it out. And if it gets bad, you call me and we can talk about medication again.”

“Honestly, I feel fine most of the time. I was thinking this morning I must be a psychopath. You know I didn’t even cry at Max’s funeral?”

“We’ve talked about survivor's guilt. Everyone’s experience is different. That’s just one facet of it. Take things slow and if you start to experience any emotional discomfort, take a step back.” She suggests, supportive as ever. 

“I will. I’m ready to just dive in. I’ve got this new position and a new apartment.” You smile, thinking about all the emerging possibilities. 

“New relationship,” she adds, as if you’ve purposely avoided mentioning it. And maybe you have. It’s not that she doesn’t approve, but she’s cautious. 

“I know you don’t think it’s a good idea, but we’re actually in a good place.”

“I never said that I thought it was a bad idea. I simply pointed out that you hold things back when it comes to him. You stop yourself from spilling too many details. Sometimes that can be a warning sign. And your work situation is less than ideal. You said he’s your boss?”

“More like...my boss’s boss’s boss. He’s at the top of the food chain.”

“Well, it’s probably better he’s that far removed.” She makes a note on her pad. “And your sex life remains one hundred percent consensual?”

“Yeah, God, you make it sound like there’s something wrong with it.”

“Again, that’s you projecting what you assume my opinions are. But I wouldn’t be doing my job if I didn’t ask. You’re certainly not the first woman in the world who enjoyed being tied up. There’s nothing wrong with it as long as it’s not having a negative impact on your self-worth or emotional health.”

“No, things are really good, all around. It sounds so fucked up to say that, but I feel like my life has a future. Is that weird? It’s not that I was sad or depressed before, but I was treading water. Now I’m going somewhere.”

“Sometimes terrible things bring necessary change. You didn’t know how to move forward here, and now you do.”

-

The new offices are two high rise buildings connected by a walkway. It’s just temporary until Sam decides on where to build the new campus but for the next couple years, this is the home of W & S. 

Glancing at the post-it in your hand you look again at the number in front of you. 

_Workspace 2852_

The office team had decided everything is now labeled as a _workspace_. There are no more offices and cubicles. Only _workspaces_ \- that look exactly like traditional offices and cubicles. You trail down the aisle, cubicles flanking the left and offices against the right hand wall. Coming to the end of the cubicles you check the paper again. You must have missed it. 

“You alright, sweetheart?” Gloria from the travel team asks. 

“I can’t find my desk. Maybe I’m on the wrong floor,” you explain.

She takes the paper from you, looking at the number and pointing to a small office tucked into the corner. “2852, right there.”

“No way,” you grin, getting closer only to find your last name scrawled across a piece of masking tape in the center of the door. 

“Sorry about the tape. The nameplates are coming, that’ll have to do for now.”

“No, it’s fine.” You’re beaming like an idiot, opening the door and stepping inside. It’s small, but the ceilings are vaulted and it’s literally in the corner of the building. Two walls are floor to ceiling windows that overlook the city below. “Shit,” you mumble to yourself, scarcely able to believe this is your little corner of the world. 

The office is naked, just a desk, computer and filing cabinet. But it’s yours. 

There’s a single, white envelope on the desk and you have a feeling who’s left it for you. Inside is a note written on the back of a business card. 

_Enjoy. You deserve it._

“Sam,” you whisper, clutching the little card like it’s a bouquet of flowers. Turning the card over you’re met with another shock. The card is yours. Your name with the title of _Department Liaison_ underneath. 

“Sorry to bother you.” A new voice and two knocks come from behind you. You turn to find an unassuming man standing in the doorway.  “I know you're probably busy. I just wanted to drop in and introduce myself. I’m Cole Trenton.”

Cole Trenton, your new boss. 

“Hi,” you beam back. He looks...nice. There’s a big smile plastered across his face as he extends his hand. His handshake is firm but not too hard, some men feel the need to crush you to prove a point but not him. “Y/N. I just got here. I’m not normally late but I couldn’t find my des- _office._ ”

“Don’t worry about it.” He waves his hand dismissing any concern. Shoving both hands in his pockets he wanders inside, looking at your view. Whistling, he looks back at you. “Someone must like you. I’m right next door, mine is bigger, but nothing like this.” 

“To be honest I thought I’d be stuck out there in cubicle land.”

“Not anymore.” He taps your desk with the back of his knuckles. “I’m not sure what your schedule looks like today, but I was hoping we could sit down and I could pick your brain. You’re my eyes and ears right?”

“Absolutely,” you affirm. “Welcome, by the way. We’ve needed someone like you for a long time.”

“I’m lucky to be here. Working for Sam Winchester was pipe dream up until two weeks ago. I just don’t wanna screw this up. I’ve heard he’s a bastard but he can make or break you.” 

“He’s not so bad,” you feel the business card burning a hole in your hand. “He just has high expectations.”

“I’m alright with that,” he chuckles lifting his hands palms forward in a sign of submission. “Let me know once you’re settled in. Whadda you say we order a pizza and go over employee files. It’ll be the first act of official business in your new workspace.” 

“That sounds great. It looks like you’ll have to bring your own chair.” You’re on cloud nine. You’ve got a boss that doesn’t hate you with his very marrow. “It’s nice to meet you, Cole.”

“You too.” He pats the door frame on the way out, leaving you truly immersed in this new beginning.  


	21. Twenty-One

It’s only been two weeks, but you decided almost immediately that you liked Cole. Not only is he smart and good at his job, he’s easy to work for. He makes it clear what he wants from you and then trusts that you’ll deliver. There’s no micromanagement or back-handed comments like Pepper. No yelling and threats like when you worked at the factory. It’s exciting to be a part of a team where everyone is rooting for each other. 

It’s a Thursday and you’re working late. With an empty studio apartment and frozen pizza waiting for you, there’s little to be excited about. It’s just after eight when you finally wrap things up, locking up your office and heading toward the elevator. 

People have settled in and each of the identical cubicles has little personal touches. You stop to look at family photos and school pictures of gap-toothed children. You wonder if you should bring in something to make your office more personal, but what would you bring? A photo of your mom?

There’s a framed photo of Sam on the cover of Forbes in the lobby and you laugh imagining it setting on your desk. Someday, perhaps, things will be less clandestine. There’s a thrill in the secret but a growing part of you longs for a slice of normalcy. 

Before you know it you have your phone out of your purse and open up the text thread between you and Sam. You hesitate before typing, then inwardly correct yourself. This isn’t your old arrangement. The two of you are in some sort of undefined relationship, but a relationship nonetheless. 

**Y/N:** Hey

**Y/N:** Are you busy?

**Y/N:** I was going to head home but-

 

Before you can finish typing the third message, Sam responds. 

**Keith Campbell:** Come over

**Keith Campbell:** I need a distraction 

 

Smiling to yourself, you respond _OK_ and put your phone away. 

“Working late?” Cole nearly scares you to death. 

“Shit!” You yelp, jumping and then laughing nervously as your heart thumps fast and hard. “Oh my God, you scared me.”

“Sorry,” Cole chuckles, hand over his heart. “I’m sorry. I thought you heard me coming.”

“I was in my own world, Jesus.” You catch your breath, as the elevator opens and you step on. “I didn’t know you were still here, I would have said goodbye.”

“I like to hunker down in my office. I do my best work when _I’m_ in my own little world.” He grins, checking his watch. “I don’t know if you’re busy but I’m headed for a drink if you’d like to join me.”

You hesitate, trying to discern if this is a pickup line or just him being a nice guy. 

“I have plans,” you explain, blushing and instantly hating the way your body always responds to even the notion of Sam. 

“Well, good to know someone has a social life. Looks like it’s just me and Nick from HR.”

Cole and Nick. He was just trying to include you. You could call Sam, tell him you really want to immerse yourself in this new professional world. He’d understand, he’s always encouraging of your development. And after all, this is a boys club and late nights at the bar talking shit and getting in good with the boss would definitely set you up for success. 

But the truth is after a long day you just want Sam. Nothing else compares to whatever he has in store. 

“Can I have a rain check?” you counter as the elevator descends to the lobby. 

-

“On your knees. Hands behind your back.” Sam’s words send a zing of excitement down your spine. 

Dropping to the floor you assume the position, watching as he digs into a drawer and removes several things that make your heart race. 

The first item is a ball gag that you’ve known he was in possession of for some time but has never used. Obediently opening your mouth, you watch each other as he secures it in place at the back of your head. 

“Good?” he asks, appraising his handwork. 

“ _Ahuh_ ,” you utter a muffled confirmation with the ball in your mouth. 

Sam has little telltale signs that you’ve learned how to read over the last year. And when he’s getting excited about the way you look, or whatever depraved act he knows is coming, his eyes narrow at the corners. Just like they are now. 

Taking a moment to appreciate the sight of your mouth stretched around the gag, he moves back to the table for his next item. 

“Hold your hands out in front of you, palms up,” he instructs. 

You immediately thrust your hands forward. He bends down with a pair of padded cuffs. He wraps one around your wrist, looping it tight, then secures the other. This isn’t like when he used his tie or belt, those you could probably get out of if you struggled hard enough, these cuffs are the real deal. There’s no escape until he frees you. 

“We’re not done yet.” He grins and your pussy clenches in anticipation of the unknown. 

These nipple clamps are new. They aren’t the simple, everyday clamps you’ve used before and seen in a million pornos. No, these are a special order. They’re little bars that tighten down as he twists a small screw. Tweaking a nipple he makes sure you’re sufficiently stiff before pulling it into the clamp and turning the screw until your nipple is on fire, pinched between the two cold metal bars. Then he does the other, leaving you staring down, feeling your heartbeat in both breasts. 

“Do they hurt?” he asks, licking his lips. He’s openly excited now, the bulge in his pants straining at the zipper. 

You nod _yes_.

“Can you take more?” he asks, dropping to his knees in front of you, eyeing your tits. 

_Yes._ You nod again. 

He turns the screw on the left clamp, a full turn that pulls a muffled scream from you as your eyes bulge out. Yeah, it’s painful but it’s wonderful at the same time. Right on the edge of too much, pushing at an invisible boundary. You can feel drool leaking from around the gag and down the side of your chin, eyes watering as you squeal again at the feeling of your nipples being crushed. 

“Too much?” he pauses, already reaching for the other. 

“Mhmm hmm,” you shake _no_. 

“Good girl,” he grins tightening the second clamp as you squirm and moan, sweat breaking out over every inch of your body. “You like this? When it hurts like this?” he asks, taunting with obvious enjoyment.  

You grunt in response, and he chuckles. His amusement spurs your shame, flushing even hotter as he reaches between your legs to check. Two fingers swipe over your sex. He doesn’t even need to get inside to feel the slick leaking from your pussy, you’re soaked and your clit is throbbing harder with every passing second. 

“Get up.” His command is accompanied by a fist in your hair as you both rise off the ground. Holding you on your tiptoes he walks to the side of the bed. ‘Bend over, arms above your head.” 

Leaning down, your aching nipples press against the mattress and you moan, wiggling in place. He walks to the other side of the bed, reaching underneath and finding a strap that’s been tied to the rail of the bed frame. There’s a clip at the end and he hooks it through the chain between the cuffs, then pulls it taught until your arms are pulled and held in place.

You rest a cheek on the mattress while he moves behind you. There’s the familiar rustling of clothes. 

You’ve talked about what comes next. Talked about limits and fantasies, but you’ve left the details up to him. All you know is you want something new and tonight it’s this. 

He spreads your butt cheeks, one hand on each cheek forcing you open for inspection. “You have such a tight ass,” he comments, a thumb prodding at your tight hole. You moan at the pressure, nipple clamps shift against the bed sending jolts of pain and pleasure out in all directions. “Jesus, I can’t even get a thumb in here right now. But you know I’m going to get my cock in here tonight. Going to open you up one way or the other.”

_Fuck._ You could probably cum just like this. 

“You know why you’re wearing the gag?” You feel the weight of him pressing down over your back, hot skin and the pressure of his body pinning you to the bed while he fondles your ass. “So I don’t have to listen to you scream when I’m fucking you. And the cuffs are to keep you in place. Can’t have you rolling around, trying to get away from me. The clamps are just to remind you who you belong to.”

You whimper, pussy twitching, clit aching from the shame and thrill at the idea of being dominated. 

“I could fuck you just like this.” Sam slaps your ass hard enough that the sting draws a yelp from around the gag. Both your butt cheeks are pulled apart again as he spits on your asshole, then forces his thumb inside up to the knuckle. 

Squealing, you pull at the cuffs as he presses his weight down on your lower back to keep you in place. 

“No lube, just a little spit and my cock up your ass,” he grits, using his thumb to pull down hard and open up the tight ring of muscle. “I know you like it when it hurts, but I’m not so sure you’d like this. But you’d deserve it wouldn’t you? You deserve to get fucked up the ass until you’ve learned your lesson?”

“ _Ess_ ,” you confirm, tears of frustration dripping onto the bed, mixing with wet spots of drool. 

“Yes,” he mimics, spanking you hard. And then he’s gone. There’s the click of a bottle and then just a tiny drop of lube on your puckered hole. It’s just enough to get him inside without any real damage but sparingly enough to make it a challenge for you. He coats his cock, fisting his length with a wet sound of skin on skin before you feel him pressing the head of his dick against your ass. “Relax and open up like a good girl.”

The sensation of his thick shaft forcing you open for him is overwhelming. He pushes forward, slow and steady as the head sinks inside. Once he’s successfully got the tip in there’s no fighting it, not even if you wanted to, as he sinks deeper and deeper, stretching your ass open and filling every last inch. 

Whining and moaning you twist and writhe at the glorious burn. The agony and pleasure always go hand in hand but this is new a level. It’s not exactly role-playing, because it does hurt and you’re bound and gagged to the point of real restraint, but it’s what you asked for and Sam was all too happy to deliver this very specific fantasy. 

“Be quiet,” he growls, pulling out only to shove his cock back in to the tilt. He finds a demanding pace right from the beginning, fucking you like the punishment you begged for. “Shut up and take my cock like a good girl instead of squealing like a slut.” 

Moaning into the gag you arch your back. His pace quickens, hips smacking into your ass with every stroke. 

“I’m gonna cum so deep in this tight little ass,” he grunts, his fist back in your hair, neck bowed backward. He’s fucking you hard enough that you’re sliding against the sheets, nipple clamps rubbing again and again. But so is your clit, it’s the catalyst you need to orgasm and your bud is grinding _just right_ with each smack of his hips.  “I’m gonna cum inside you just like this. Fill you up and watch it drip out of you. I better not feel you cum. Don’t you dare cum, you hear me?” He twists your hair even harder, scalp burning. “This isn’t for your pleasure. Only a whore would cum from getting fucked up the ass.” 

Everything about this moment is working in tandem. Being gagged and unable to speak, the cuffs keeping your arms stretched and helplessly immobile. Then the pain of the clamps biting your nipples and clit rubbing the sheets. And all of this while he’s fucking your ass like a whore, talking to you like you deserve it. This is every fantasy you’ve ever been ashamed of all at one time. 

“Fuck,” Sam groans, fucking faster and deeper. “Open just like that...gonna cum just like this.” He grinds deep and shoots inside you, warmth spreading as he spurts his thick seed “Don’t you dare fucking cum!” he demands again, slapping your ass while he’s still emptying. 

And that’s all you need to cum right along with him. Your empty pussy clutches and spasms, tight hole bearing down on his cock as if sucking him even deeper. It’s wave after wave of orgasm, coming in a flood of satisfaction that nearly drowns you. Each pulse, every flutter, brings a new bliss. Your eyes roll back into your head and you ride out the most intense orgasm of your life until you’re boneless and panting around the slippery ball gag. 

“Fuck.” You hear Sam sigh, holding himself deep for one last moment and then _oh-so-slowly_ pulling out, inch by agonizing inch until you feel the head catch and then you’re empty. His hands hold your cheeks apart, watching until cum finally begins to drip out and he’s satisfied. 

His first order of business is to unbuckle the gag, he quickly slips it off as you gasp into the bedding, finally able to take a satisfying breath. 

“Rollover,” he instructs quietly. 

The chain attached to the cuffs twists as you move onto your back, looking at Sam above you. His face is flushed, cheeks a deep shade of red and sweat beaded on his forehead. He smiles softly, eyes fluttering down to your breasts to release the nipple clamps. First one, then the other. The blood rushing back hurts more than the clamps themselves. You’re overly sensitive but that doesn’t stop him from sucking on each one until they’re no longer purple and swollen.

The cuffs are the last to come off, he silently frees you and then sits on the edge of the bed as you get up on your knees, rubbing a wrist. 

“That was amazing,” you grin, leaning forward to kiss him. “Thank you.”

“You’re welcome.” He cups both your breasts, thoughtfully rubbing thumbs over each nipple. You close your eyes, enjoying his touch and the wet feeling between your legs. “Are you staying the night?” 

When you look he’s staring expectantly, his gaze darting to your mouth. 

“It’s a weeknight,” you put up a protest but it’s all show and you both know it. “Do you want me to stay?”

“Yes.” 

It’s a single word, spoken definitely and without hesitation. That single _yes_ feels like a thousand other unspoken words, all the things left to be said. 

 

**The Next Morning**

“Last night was perfect,” you grumble happily as his arms slide around your waist until you’re flush against him. “Exactly what I needed.”

You came into the kitchen hoping for toast and jelly but Sam quickly sidetracked the search. 

“I’m glad to hear that.” He smiles back, blinking at you, lost in his own thoughts before leaning down to kiss you. “I didn’t do any lasting damage?”

“Not even close.” This whispered confirmation is met with another kiss, and then another. It’s not even seven and you’re ready for more of him. “You know, we’ve done other stuff in here, but you’ve never fucked me in your kitchen.”

“You are correct” Two hands cup your butt cheeks, squeezing before easily lifting you into the air. “Luckily, that’s a problem I have a solution for.”

“I love immediate resolution,” you laugh as he sets you on the counter, wedging his hips between your legs. You scoot forward until your bare pussy is grinding against the erection straining through his pajama pants. 

“You want me to cum in your pussy or your mouth?” He pulls back, thoughtfully awaiting your response as his thumb slides past your lips and you eagerly suck on it. 

“My pussy,” you confirm, as his spit-wet thumb hooks over your bottom lip before letting it pop free.

“That’s a good choice.” He yanks the shirt over your head, leaving you stark naked. Hooking one leg over his hip you press your heel into his ass, letting his covered cock feel just how eager you are for some morning sex.  One hand cups your breast, the other is in a fist at the back of your hair holding his mouth against yours. 

Then, out of nowhere, comes a voice so out of place you’re not sure you even hear it. 

“I did the best I could, I swear. Mohamed said he can - Oh my god!” Pepper’s voice ends in a high pitched declaration. She stops in her tracks, the folder in her hand tumbles to the floor as papers skim out like water bugs across the tile. 

Sam pulls away from you and you both stare at her, dumbfounded by the intrusion. His hand falls from the back of your hair, using his thumb to wipe away the spit you’ve left on his lips. “I don’t remember asking you to come by this morning, Pepper,” he delivers evenly as if she hasn’t just walked in on the two of you. 

“I’m so sorry, sir. I had the driver let me in, I didn’t think - I’m so sorry.” Her eyes stutter from Sam to you. You watch as the realization dawns on her. The sight of Sam and a naked woman in his kitchen was shocking enough, but then she recognizes who said woman is. “Holy fuck,” she whispers, her mouth falling open. 

The shame is immediate, and not the good kind you get from Sam’s dirty little tasks. Throwing an arm over your breasts, you point to the shirt on the ground behind him.  “Can you hand me my t-shirt please?”

He looks from Pepper to you, then leans down to pluck it off the floor. You pull it on, getting ready to hop off the counter and go hide in the bedroom, but he stops you with one hand on your thigh. “Stay where you are.”

You look from Sam to Pepper, turning a darker shade of red, but sit there waiting to see how this is going to play out. 

“Why are you here?” he turns to Pepper. 

“I, um-” she can’t stop staring at you. “I forgot to have you sign the Lexington papers last night. And they won’t allow anything done by electronic filing. I needed to hand it off to the courier by nine and you said you’d be in late today.”

“You couldn’t knock?” he raises an eyebrow, still cool as a cucumber. 

“I did knock. And I called your name, but you, um, didn’t hear me,” she sputters, looking from you to the floor, anywhere but at Sam. 

You’ve never seen her like this before. In the presence of Sam’s disapproval, she’s a mouse, scared and cowering. 

“Well, what do I need to sign?” Sam cocks his head and Pepper drops to her knees, collecting strewn documents. 

“Um,” she’s frantically searching through the papers. “Sorry, I’ll find it.”

“Sorry is a useless word,” he spits back and you get a glimpse of the Sam that everyone talks about. The difference is when he talks to you this way, you get turned on. But as you watch her on the verge of tears, you start to feel bad for her. “Get yourself organized.”

She finally finds what she needs, setting the papers on the counter and then fishing for a pen in her bag. Her face is red, eyes darting to you, then looking away. 

Sam skims each page and signs, handing the pen back to her. 

“I’m sorry,” she offers breathlessly, voice shaking while she looks in horror at Sam. “I mean, I’m-”

“Next time you’ll call. If you can’t get a hold of me, you wait. Don’t come to my house,” Sam orders, both hands on his hips. 

“Yes,” she nods, staring at you as if you're a zoo animal.

“And Pepper,” Sam takes a step, pulling her focus from you to him. “You’re not going to tell anyone about Y/N.”

“Of course not, sir,” she nods aggressive, eyes going wide. “Of course.”


	22. Twenty-Two

 

“Are you seriously going to pretend like that didn’t happen?” You trail Sam back down the hallway, glancing behind you. Pepper ran out as soon as she collected her documents, but you’re still on edge. 

“I’m not pretending anything.” Sam wanders into the bedroom, waving a hand without turning around. “What reaction would you like me to have?”

“I don’t know,” you stand the doorway, trying to think coherent thoughts. “You’re not concerned? Embarrassed?”

“Why would I be concerned?” He pauses to turn back to you skeptically. “She won’t tell anyone. She’s a bitch and she hates you but she would never betray my trust.”

“Oh,” you nod, unable to believe how calm he is. “So that’s just it huh?” 

“Why would I be embarrassed?” He cocks his head, asking it as a genuine question. 

“I don’t know,” you shrug. “She walked in on us having sex. In your kitchen.”

“You’re the one who was naked. I understand why you'd feel that way,” he volleys back. 

“And it’s not a thing for you?” you inch into the room. “That she knows you’re with me or sleeping with me at least?” 

“You say that like you’re something to be embarrassed about,” he snorts, yanking his shirt off over his head. “I’m sure most people would think being with you is the best part about me. My sole redeeming quality.” 

And with that, he wanders off into the bathroom and shower turns on. You smile to yourself, cheeks burning at his easy declaration. He always does this, says things that would be laughable if it was anyone other than him. 

“Take your clothes off and get in here,” he calls from the shower. 

“Coming!” you sing-song, shedding your shirt and joining him under the warm water. 

His kisses are messy this morning, open mouthed and wet, the heft of his tongue sliding over your own. You find yourself trapped between his warm, dripping body and the cold tile of the shower as he lifts you up and slides his cock into your pussy in one easy move. 

The first thrust is always the best, that forced stretch of your body opening up for him and the thickness of his cock filling up every last inch inside. One of his forearms presses on the tile beside your head, the other hand cupping your ass, as he ruts up into you again and again. 

“Fuck, Sam,” you moan into his mouth. Grasping his shoulders you hang on as he thrusts hard and fast. 

He stops to nip at your bottom lip, catching it. “We’ll try this in the kitchen again this weekend.”

-

You haven’t been up to Sam’s office since W & S moved into the new buildings. The old offices were modern, but these buildings are from the turn of the century with an aging charm you can appreciate. 

With a controlled, neutral expression you approach Pepper at her desk. She glances up, sees you and then looks back to her computer. 

“He’s out to lunch with a client,” she explains coolly. 

“Actually, I came to see you.” 

“Why?” She smiles, a frightening expression that’s so unnatural you almost flinch. 

“You know why,” you whisper, stepping closer. “I just wanted to say I’m sorry that you walked in on us. It had to be really uncomfortable seeing us like that, seeing Sam with me.” 

“Please, don’t patronize me. I’m an adult. I can handle seeing your tits,” she spits back, her cheeks turning red. “Are you honestly naive enough to think you’re the first? Two years ago I caught him getting a blow job in the middle of his living room. You, naked in the kitchen, doesn’t even rank compared to that.” 

Stifling your reaction you take a step back from the desk. She invoked the idea of Sam with another woman to get a rise out of you but you refuse to play into her game. “I shouldn’t have come up here. I’m sorry.”

“You, of all people,” she mutters, unable to hold back. 

“What the hell does that mean?” you counter. 

“I mean, I get it,” she sneers. “You’re beautiful and good at taking orders, he likes that. But Jesus, how did the two of you even get to that point? What, did he save your life and so you felt like you should offer him your pussy?” 

“What’s wrong with you?” You stare at her, trying to determine the root of this hostility. Does she want him? Does she just hate you that much?

“Just be sure to watch yourself,” she warns. “I thought he was too smart to hook up with some desperate woman at work but I guess all men are led around by their dicks after all. If you think you matter to him, you don’t. I’ve seen that side of him, he’ll fuck you until he’s had his fill and then you’re toast.”

“Why are you always so nasty?” Shaking your head you back away. You came here to offer an olive branch but she’s not going to allow that. 

“Because I’m the one who put in the time!” She points at you, thrusting a finger forward. “I work ninety hour weeks. I take his shit day in and day out, I take the blame and responsibility for every Goddamn thing that goes wrong. And you suck his dick and now you’re in some made-up position making the same amount of money as I am but dealing with a fraction of the bullshit. Jesus! Honestly, you were the last person I thought would sleep her way to the top. I didn’t think you had it in you.”

“It’s not like that,” you counter, wiping away a tear that’s managed to escape. 

“What is it like then?”

“It’s not how you’re making it out to be.”

“How many blow jobs get you a position like that?”

“Now you’re just being cruel.” 

“I’m being real.” Her face is beet red, her eyes welling up with tears. “You’ve been here a year and he’s given you special treatment from the beginning. I can’t stand to look at you anymore. I’ll send you an alert via email when he’s back in his office if you want to see him.”

-

Hours later you’re still seething from the confrontation. You’ve been locked up in your office, practically vibrating with anger since the encounter earlier that morning. Pepper has always been a grade-A bitch and you should have known that trying to explain yourself would get you nowhere. At least Sam was right about one thing, you’re sure of her allegiance. She takes her position seriously and she’s terrified of him. That makes for a powerful combination. 

You’re about to go over next week’s schedule when there’s a knock on your door. Looking up you find none other than Pepper. Rolling your eyes you shake your head _no_ , glaring at her. 

“What are you doing here?” 

Pepper leans against the door frame, watching you intently before stepping inside and carefully shutting the door. She silently takes a seat across from you, sucking in a breath before speaking. 

“I was thinking. When you were leaving for Chicago, Millie wouldn’t shut up about your mystery boyfriend. She went on and on about what an asshole he must be to make you leave the city just to get over him. She thought it was Dale from accounting.”

You shift in your chair, uncomfortable with where this is going but even more appalled at the idea of Dale being your lover. 

“He’s like, sixty.”

“Yeah, but a silver fox,” she grins. “Then I started thinking about Sam’s special project. All those last-minute meetings. In the entire time I’ve worked for him, he’s never once scheduled a meeting himself. I should have known there was something going on.” 

“I wasn’t trying to get special treatment. It just kind of...evolved,” you admit quietly. “It was never my intention to use him to get ahead professionally. Despite what you think, that’s not what this is. I’m good at this.”  

Her eyes narrow as she studies you. She’s clearly been working with Sam for too long because she’s taken on several of his mannerisms, including his stare that could pry state secrets out a cold war spy. 

“When did it start?” she asks. 

“That is none your business,” you counter, suspicious of her motives.  

“Oh come on,” she sighs dramatically, leaning back in the chair. “Who am I going to tell? I signed a nondisclosure when I started working for him. If I ever spill any of Winchester’s beans he’d ruin my life.”

It’s an interesting juxtaposition. You and Pepper have more in common than most. Your varying relationships with Sam and the sex contract he made you sign. It’s strange to hear her talk about their own legal agreement. Sam knows the devil is in the details and he’s covered his ass from all angles. 

“It happened early on,” you admit, feeling a weight lifted in telling someone, anyone. Even if that person is your arch-nemesis. “When you first had me cover for you during that snowstorm.” 

“Shit,” she breathes looking at you in a mix of disbelief and amazement. “You’re sleeping with Sam Winchester. I don’t get it. I mean, women like power but this is Sam we’re talking about. Does he give you his frequent flyer miles or something?”

“If you’re going to be like that, you can leave.” You point to the door and she rolls her eyes. 

“I just mean, it’s crazy from both sides. I always figured he hired high priced hookers or something, but you...I can’t believe I didn’t see it. Does he pay you?” 

“Fuck you, Pepper,” you sneer, leaning forward. “I’m not a whore.”

“What? Are you dating?” She laughs at the idea. 

You offer a shrug, then nod slowly in confirmation. 

“Are you kidding me?” Her face falls, a look of genuine concern pulling her mouth into a nasty little grimace. “Do you live with him?”

“No, I mean I stayed for a while after the shooting, but I’m not living there now.”

“I don’t even know what to say.” All the energy has drained out of her. 

“Why is it so hard for you to believe that he would be with me?”

“It’s nothing to do with you,” she shakes her head. “I mean, I know he’s not a machine but he hates people. I can’t believe he would have the patience to be in any kind of relationship. You gotta be a masochist because he’s a bastard.”

“He’s not so bad,” you retort. 

“Fuck, you got it bad for him, huh? You clearly haven’t been on the receiving end of that temper.”

Your face goes hot, and you swallow hard at the mere idea of being on the receiving end of anything he’s got to give. 

“He can be sweet.” You smile to yourself and glance up. Her eyes have shifted, a sudden hesitation crossing her face. 

“Please don’t tell him what I said,” she requests in a hurried breath. “What happened with the documents, that wasn’t my first fuck up recently and I can’t get fired, please don’t tell him. I know I’ve been a cunt to you, but I need this job. No one is going to pay me close to what he does and I’ve got people in my life who need that money. Please don’t tell him.” 

“Okay,” you agree automatically, watching the desperation wash over her entire demeanor. There’s clearly a lot more going on with Pepper beneath the surface. “I won’t.”

“Why wouldn't you?” she snips. “If what you said about your relationship is true, he’d be furious if he knew I talked to you that way. After everything I’ve done to you, why would you keep your mouth shut? I’ve thrown you under the bus a couple of times.” 

“I’m not you, Pepper.” You shrug. “It wouldn’t make me feel any better to get you in trouble. Not to mention we both almost died. I think that means we deserve a chance to start over. I’m not saying we need to be friends, but at least we can be kinder to each other.”

“Alright,” she agrees hesitantly. Rolling her eyes again she laughs, shaking out nervous energy. “I can’t believe this.”

“Sam thinks a lot of you,” you add and she snaps to attention. “He trusts you and we both know there are not many people on that list.” 

“Well,” she shrugs, getting up and head to the door. “I wish someone would tell him.”

-

Cole’s office is exactly what you expected, meticulously organized with small personal touches that make it his own. He spends most of his life here, countless hours working hard to make a good impression and so far he’s exceeded everyone’s expectations, including yours. 

Behind his desk, on a floating metal shelf, are multiple photos. One of him in military garb with his former unit. Next to that is a photo of an older couple you assume are his parents. Mounted on the wall are his degrees. There’s a NorthWestern diploma for his undergrad and then his law degree from Georgetown. 

He’s incredibly proud of his history as a Marine and you wonder why he left the service. He went to school later in life than most but he’s certainly excelled. He’s roughly the same age as Sam, maybe a few years older but just as disciplined. 

“Sorry I’m late.” Cole shakes his head, closing the door to his office and dropping a stack of folders onto the desk. “I had a meeting with the big guy.”

“How did it go?”

“Good,” he looks at you thoughtfully. “I think. He’s hard to get a read on.”

“That he is,” you agree.”But I think you’d know if he wasn’t happy.”

“I mean he doesn’t pull any punches but that's how I like to work. Let’s just try and not screw up, okay?”

“I’ll do my best.” You give him a little salute and he chuckles. 

“We’ve got a client, it’s an intellectual property rights case and we’re representing Lavion. In fact is looks like moving forward we’re going to represent them exclusively.” 

Lavoin is a tech giant, right up there with Google and Microsoft and it’s owned by none other than your biggest fan, Nick Luster. They’re still considered an up and coming company, but in a few years the talking heads expect Lavion to surpass their current competitors. 

“That’s huge.” It’s a strange thing to feel excited about work, this is a first but you can’t deny how fulfilling it is to be part of a powerful team like this. “What’s our role in this?” 

“There are 162 members of the legal team that are available for assignment or reassignment. Our task to determine what ten associates we’re going to assign and then oversee the case. Eventually, we’ll oversee everything, all the junior associates at least. But it starts here.” 

“Holy shit,” you breathe, grinning at each other. 

-

Your period runs like clockwork. It comes on the same day, at the same time, every month without fail. It should have started this morning, but when you checked the pantyliner during lunch it was pristine white. 

There’s a sick feeling in your stomach as you double-check your calendar. You’ve never been late, not for years. 

A day later you’re starting to panic but realize it’s time to man up and find out, so you head to Walgreens and pick up a two-pack of pregnancy tests, tucking them into your purse before you head to Sam’s house for the weekend. 

He’s not home yet when you arrive. You lock yourself in a guest bathroom, deciding to make double sure of the results. You pee on both, then set them on the counter and set the timer on your phone. 

There’s never been a longer five minutes in the history of the planet. You take this time to contemplate how little you know about Sam and how a tiny pink + sign could change the trajectory of your whole life. You don’t want children, not right now and definitely not with a guy that only confessed his feelings after you were confronted with certain death. Sam, especially in his current state, is not exactly father of the year material. 

The timer on your phone sounds and you take a deep breath, shaking out your hands to release the nerves before looking. 

Negative. 

And a second negative.

“Fuck,” you whisper, laughing in sheer relief. “I’m such a drama queen,” you mutter to yourself, taking the tests and grabbing your phone. 

You’re halfway back to the bedroom when Sam appears in the doorway, pulling the knot of his tie loose. He looks amused, smiling at you. “Where were you? I saw your purse in the kitchen…” 

His voice trails off as he hones in on the tests clutched in your hand. His face drains of all color, just as panicked as you were earlier. 

“Don’t worry,” you take a step toward him. “I’m not pregnant, my period is just late. I scared myself too.”

“Good,” he blinks, collecting himself. Pausing he starts to say something and then stops himself to reconsider the delivery. “I don’t want children.”

“Me either,” you agree. “Not right now, anyway.”

“Ever,” he clarifies. “You should know that, if it’s a non-negotiable for you.”

“Oh.” You’re stunned for a moment, taking in this declaration. First, it’s a pretty ballsy thing to say to your non-girlfriend girlfriend just minutes after she thought she might be pregnant. On the other hand, he’s talking about this information like he intends for your relationship to progress into the long term. “I’d prefer if you don’t use business jargon when we’re talking about personal matters. It’s not something I’ve thought much about. I’ve spent my adult life trying _not_ to get pregnant.” 

“Good,” he confirms, staring at you with uncomfortable intensity. Is this his ultimatum? A challenge? Whatever he’s trying to convey it has you on edge. 

“What would you say if I told you I _was_ pregnant?” you counter and he recoils, a grimace pulling at his lips. “You wouldn’t want me to have it, would you?”

He swallows, jaw tightening as he takes off his glasses. Taking a breath he remains collected and looks at you dead on. “It would be your choice of course, but _I_ don’t want children.” 

“Will you tell me something, Sam?” You inch closer, keeping your reaction in check. “Do you see us in a place where that would become an issue? I mean, when you think about our relationship, are we together in a year? Five years? What does the future look like for you.”

“I don’t deal in hypotheticals,” he quips dryly, suiting up in his emotional armor. 

“We’re not wheeling and dealing in anything. We’re talking like two people who care about each other. I’d like you to answer my question.” 

“Jesus Christ,” he mutters, rolling his eyes and turning to walk back into the bedroom. You’re about to really let him have it for walking away but he sits down in the modern, upholstered chair tucked into the corner. “If I’m lucky, which I doubt will happen because the universe fucking hates Winchesters, but if I’m lucky in five years you’re still with me. Maybe we’re living together. But if you really want to know what we look like in the future, I’ll tell you what’s going to happen. You’ll be as far away from me as you can get. I’ll hurt you. I’ll make you regret that you ever gave me a chance. You’ll move on to find a happy life with some accountant from Idaho who thinks he’s won the lottery.” 

“That’s bleak,” you respond immediately. This isn’t the first time he’s expressed his belief that he’s going to drive you away. “You know what I think? It’s an excuse for your shitty, closed off behavior. If you keep saying in the end you’re going to make me hate you, it’s just a self-fulfilling prophecy when it happens. You get to act like a dick, refuse to open up and when I leave, _well fuck_ , you’ve known it would happen all along. Stop being such a coward and let me in. You’re using this bullshit premonition of our inevitable demise as a reason to not let me know you.”

His nostrils flare out, eyes narrowing. He hates being called out, but you’re not done yet. 

“Maybe I will want to have a baby one day, but I can’t make that decision right now. I can’t even start to think about that because we’re still learning how to become _us_. I want to know you, to fall in love with you, hell maybe I already am in some twisted way, but I don’t know that yet. Maybe we’ll hate each in other in five years, but there’s also a chance that we really fucking enjoy each other too. Maybe we get married and adopt a dog. My point is I don’t fucking know what’s going to happen and you don’t either. So stop acting like you can see the future and just open up a little and be here with me. Show up _now_ , Sam. I’m waiting for you, I want you. All you have to do is try.” 

He’s silent, his jaw set with each hand resting on either thigh. His eye twitches, mouth pulling in discomfort. 

“I think about you all the time.” He delivers this as if he’s making a weighty confession of some tawdry affair. “It’s been hard for me...for a long time...to concentrate on anything good in life. In my experience, the things I care about always have an expiration date. I don’t deal with loss well. The more I care about you, the greater that loss will be for me.”

“Sam,” you walk over to him, kneeing your way onto his lap. His hands slide over your hips as you look down at him. “What if there is no expiration date? What if you don’t lose me? You are the only one running away.”

“I’m not good at this,” he snorts, thumbs sinking into the meat of your waist. 

“Well, lucky for you that isn’t news to me.” You pat his chest, looking over this handsome face you know all too well. “We should go on a date. Like a normal, real people date.”

“A date?” He raises an eyebrow.

“Yeah, you know, dinner and a show or something normal.” 

“What if someone sees us?”

“Well,” you shrug. “We can’t hide in the shadows if we want to move forward. I’m not ready to shout it from the mountain tops that I’m sleeping with my boss’s boss. I’d be happy for everyone to know that I’m with you, it’s the assumptions people will make that give me pause. But this is more important than my ego. If people find out, they find out.” 

“I’ll make a reservation,” he shrugs. 

“Good,” you nod, leaning down to kiss him, but pull back before your lips meet. “There’s actually one more thing I wanted to talk to you about.”

-

“Pepper!” Sam calls through the open doors of his office. 

He normally uses the intercom; when he hollers it means she’s about to get it. Pepper scrambles out of her chair and into his office, pulling her blouse into place. He sees her as an extension of him and when she looks less than put together he lets her know. 

“I’m here,” she stands up straight, hands clasped together. 

Sam’s standing in the middle of the room with both hands in his pockets. Never a good sign when he’s out of his seat. It means he’s got energy, something has riled him and she takes the brunt of his mood swings. 

He stares right through her, eyes narrowing, the two of them locked in silence. 

“It’s been brought to my attention that you had quite a conversation with Y/N.” 

This statement sends her heart into her stomach. _You bitch._ You said you wouldn’t tell him but she should have known better. 

“Y-yes,” Pepper stammers. 

“I’ve also been advised that you feel you’re more qualified than Y/N for the position under Cole Trenton.” He lifts an eyebrow awaiting her answer. 

She’s not normally a crier but life has been harder than usual lately. 

Pepper feels like she might throw up. She’ll never forgive you for this. A single tear falls down her cheek but she wipes it away immediately. He hates it when people cry and she doesn’t want to make this worse. 

“I-I said something I didn’t truly mean,” she offers, voice wavering. “I’m sorry. I should never have said anything.”

“No,” he shakes his head, walking leisurely back behind his desk. “You shouldn’t have.” 

 _Here it comes._ She closes her eyes and prepares for one of his monologues on her many failings and her impending termination. 

“There are two reasons that you aren’t a fit for that position.” He sits down in his chair, leaning back and resting a forearm on the desk. “One, no one wants to work with you. Even if you and Cole worked well together, I needed someone that people like. Someone people will talk to. It’s a liaison position, I can’t have a person in that role who’s burnt as many bridges as you have.”

“I understand,” Pepper whispers, staring at the carpet. 

“Look at me, not the floor,” he snaps. Pepper gulps, clearing her throat as she lifts her chin. “The second reason is that _I_ need you. No one else is capable of doing what you do. You balance my schedule, you understand the differing levels of importance when it comes to people, meetings, and tasks. You’ve managed to work directly for me for years without cracking. I trust you and the number of people I trust I can count on one hand. You are invaluable to me.” 

She’s stunned, she stands there staring at him, no longer shaking but in complete shock. He doesn’t offer praise, especially not to her. 

Sam taps a file on his desk.

“Your mother’s been sick.” He’s not looking for confirmation. He already knows the details. “Now your brother has been injured.”

Her mother’s been sick for a while, slowly dying a painful death in a hospital bed in Ohio with no insurance. Her brother, Dan, went to check on their mother every day. But last week he was in a car accident, he’s in intensive care. 

Now it’s just her. 

“Yes,” she stares at him, wondering where this is going. 

“Do you need to go home?” 

“I...I don’t know.”

“You should go.” He waves his hand at her. “When you’re at work I need you to be on your game. If that means you need to handle what’s happening with your family, then go and take care of it. Be with your family and come back when you’re ready.” 

“My mom, um,” she wipes her eyes again. “I was waiting until she was closer to the end to ask for a leave. It could be a month, maybe longer.”

“I understand that.” Sam stares at her, emotionless and stoic. “Find a suitable replacement that won’t turn my life upside down. Take as long as you need.”

“Thank you,” she whispers, already backing out of the room before he changes his mind. 

“Don’t thank me. It’s selfish. I need you long term. When you get back we can discuss your salary.”


	23. Twenty-Three

**Forbes:** At 30 years old you ranked as one of the top 25 most successful men in business.  You are a huge success. You’ve done all this by the seat of your pants, with no particular training in management. How did you learn how to run a company?

**SW:** You know, throughout my years in business I’ve discovered something. Coming up, I would always ask “why do you do it that way?”. The answer I would invariably get is: “Oh, that’s just the way things are done around here.” Nobody knows why they do what they do. Nobody thinks very deeply about processes. That’s what I’ve found.

In business a lot of things are folklore. They are done because they were done that way yesterday. And the day before. You have to dig in, ask questions, and not be afraid to piss people off.  It’s not the hardest thing in the world. It’s not rocket science.

**Forbes** : What drives you?

**SW:**  As a kid, I read an article in Scientific American. It measured the efficiency of locomotion of various species on the planet. Bears. Chimpanzees. Raccoons. Birds. Fish. How many kilo-calories per kilometer did they spend to move? Humans were measured too. And the condor won. It was the most efficient. Humankind came in with an unimpressive showing about a third of the way down the list. But somebody there had the brilliance to test a human riding a bicycle. We blew away the condor. Off the charts.

This really had an impact on me. Humans are tool builders and process creators. We build things that can dramatically amplify our innate human abilities.

If you set a vector off into space, and you change its direction just a little bit at the beginning, the difference is dramatic when it gets a few miles out in space. If we can nudge it in the right direction, it will be a much better thing. I think W & S has had a chance to do that a few times. That gives me tremendous satisfaction.

**Forbes** : What drives Winchester & Singer employees?

**SW:** Most people don’t get a chance to do that many significant things in their life. I’m offering people the chance to be on the forefront of change. Everyone person is handpicked to be here. They could be sitting in a monastery somewhere in Japan, or out sailing. Some of the executive team could be playing golf, they could be running other companies. Everyone at W & S chosen to work with this emerging corner of law and technology. Plus I pay people what they’re worth. A rock star deserves a salary to match. I’ve never shied away from rewarding those who deserve it.

**Forbes:**  Let’s just get it out there, the elephant in the room. How has the shooting changed the way you run W & S? What would you do differently in hindsight?

**SW:**  The most effective change I’ve made has been hiring outside managers to monitor each department’s cultural cohesion. I hire the best and brightest, with that comes egos, reputations, and unrealistic expectations. It’s a balance between heavy-handed micromanagement and understanding what’s truly going on. We’re placing a greater focus on not only the quality of work produced, but the quality of the work experience.

**Forbes:**  You’re a notorious figure with a demanding reputation. How do you see yourself?

**SW:** My job is to not be easy on people. My job is to make them better. My job is to pull things together from different parts of the company and clear the way and get the resources for key projects. To take these great people, push them, and make them even better, coming up with more aggressive visions of stale concepts.

**Forbes:**  What advice would you give to someone looking at you as their model for success?

**SW:**  Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. You’ll know when you find it. Your time is limited, so don’t waste it living someone else’s life. I learned that the hard way.

**Forbes** : You’re known for being stubbornly private regarding your personal life, but in one of your most famous quotes you said things such as hobbies and even family were a distraction. You’re older and wiser, do you still believe that?

**SW:** (long pause) Yes, but there’s someone in my life now who won’t be too pleased with my answer. The right partner makes you better. Distractions can turn into strengths, but I still believe it’s important to screen who and what you let into your life.

 

You sit back on the couch smiling at the photo of him on the opposite page. The photographer managed to make him look like some kind of billionaire playboy. He’s wearing a designer suit, something edgy and slim with no socks and leather shoes. His trademark glasses are nowhere to be seen and his hair is wild around his face. He looks like a different Sam, a doppelganger from another universe.

This is his second Forbes cover. The first showcased him as a new powerhouse executive but this article goes on and on about the way Sam is reshaping the way law will be written as it regards to intellectual property rights.

And that last question and then his answer. The right partner makes you better. You wish he was here in your tiny apartment so you could crawl into his lap and show him just how much better things can really get.

 

**Monday**

On Monday morning you follow Cole to the nearest conference room. You’ve worked hard to put together the right team for this maiden case. Everyone is feeling the pressure, pressure that’s only made worse by Sam’s attendance.

Sam makes you slightly nervous, but only because you want him to be proud of your work. Truth be told you’re more concerned about proving to Cole you can do this job and do it well.

Everyone else is terrified of incurring the wrath of the great Sam Winchester.

Despite working for W & S most employees never meet him face to face, so this is a big deal for the team and even more so for Cole. They have a lot to prove. This morning is the first in a battery of tests to come.

You set up the presentation while the team trails in. Each junior associate has been assigned an assistant and you’re happy to see the familiar faces of Millie and Lexie.

“Is he normally late?” Cole glances at his watch. “It’s 9:15.”

“No, not normally,” you reply as the door opens and a blonde woman you’ve never seen before scurries in ahead of Sam. The look on his face tells you everything you need to know, something didn’t go his way. He’s pissed.

He takes a seat, opening a legal pad full of notes. The woman sits beside him, offering a pen. He sighs and plucks it from her fingers.

“Let’s get started.” Sam begins. The room is so quiet you could hear a pin drop.

“Right,” Cole stands up, adjusting his suit jacket. “I’ve put together an overview, the key players and areas we believe there’s wiggle room to make our case.” He turns to you on cue. “Y/N.”

You start the presentation from your laptop, doing everything in your power not to look directly at Sam.

Cole presents, he’s well spoken and thinks on his feet. Sam interjects with questions designed to test Cole’s agility as much as hear an answer, but your new boss performs just as expected.

Next up are the associates and they don’t fare as well. Leon hasn’t done his homework, he doesn’t have the correct cases with the legal precedent. Jasper looks like he’s going to throw up as Sam goes down his list of suggestions and eviscerates each one, piece by piece.

While Sam speaks it occurs to you for the first time perhaps this is less his intolerance and more about the frustration of being the smartest person in the room. He already knows the answers, he doesn’t make a move without planning five steps ahead. He’s just trying to get everyone else caught up.

Halfway through his interrogation of Jenny Salter, a leggy redhead who started two weeks ago, the soft strains of a radio can be heard, growing closer. The guy who runs the coffee cart listens to classic rock on a little radio as he wheels around the office and at the moment Blinded By The Light is getting louder and louder.

“What the hell is that?” Sam cocks his head.

“I’ll go check,” Millie gets up.

As you watch her stand up your heart flutters. Little palpitations, once, twice, and then a tightness spreading out. Shit. This couldn’t be a worse time.

Your palms go sticky-sweaty, a heat starting in your belly and fanning out like wildfire, until it seems the walls are closing in.

“Can someone help her,” Sam gestures toward the open door. “Is it that difficult to turn a radio off?”

“I need to get out of here,” you whisper, grabbing Cole by the wrist.

“What’s wrong?” he whispers back, turning to look at you. “Jesus, are you sick?”

“I just, um…” the words get caught as your breath goes choppy. “I can’t breathe.”

“Are you okay?” Jenny inquires from across the table. Under any other circumstances, you’d be horrified to have all the attention focused on you but right now you’re desperately trying not to pass out.

“Y/N?” Sam’s voice drifts in from somewhere far away.

“I’m gonna…” are your last words as everything fades to black.

-

You blink once, twice and a third time cobwebs begin to clear. There’s a pounding in the back of your skull, a heavy _thump thump_  that hurts like a motherfucker.

It takes a moment to place the location but you’re lying on a couch in Sam’s office. When you turn your head both Sam and Cole are standing near his desk, both of them watching you.

“Welcome back,” Cole smiles, moving forward. You lock eyes with Sam for a moment, before focusing on the other man in front of your.

“I passed out huh?”

“Yeah. You hit your head on the table on the way down. You’re gonna have a goose egg.” Cole makes a pained face.

“Shit,” you feel at the tender lump on the side of your head. “This is so embarrassing. Sorry I ruined the meeting.”

“Nothin’ to be sorry for.” Cole nods. “You should probably go get checked out.”

“It’s just a panic attack. I get them from time to time. PTSD.”

“I’m familiar.”

Of course he is, the man fought in a war and you’re talking to him about PTSD.

“You should go home,” Sam suggests, studying the interaction between you and Cole.

“Really, I think I’ll be okay. I’ve got some work I need to finish-”

“Go home.” Sam raises his voice. It’s not a suggestion.

“Probably a good idea.” Cole agrees. He offers you a hand up from the couch. “You live close? I can-”

“We have people who can take her,” Sam interjects. “I’d like if you would go back down and pull everyone back together. Have the team regroup and we’ll reschedule for this afternoon.”

“I’d kinda like to stay with her.” Cole looks to you. “I feel responsible.”

“I’ll watch her until a driver comes to take her home.” Sam holds out his arm, ushering him toward the door. Cole looks hesitant, but nods in agreement.

“Check in later and let me know how you’re feeling okay?”

“Sure thing.” You’re thankful for his kindness. He’s proven himself to be an upstanding guy. You’re lucky to have him as a direct supervisor.

As soon as the door clicks shut Sam is kneeling on the carpet in front of you. One hand slides into your hair, finding the growing bump.

“Ouch,” you hiss.

“It’s big,” he cautions. “You should have a doctor look at it, make sure you don’t have a concussion.”

“I passed out before I hit my head. I think I’m fine.” You force a weak smile, looking over his face as he looks up to you.

Sam rarely looks up at anyone or anything, this position is vulnerable, submissive but he doesn’t seem to mind as he studies your face.

“It was a bad one,” Sam denotes. “It came on fast and you were on the ground in under a minute.”

“So embarrassing.” You watch him as he carefully pushes hair away from your forehead. “Do I have to go home?”

“Yes,” he maintains. “Go to my house.”

“Really, I’m okay. I can just go to my own place and lay down.”

“I’d like to check on you later. I’d prefer if you stayed with me.”

You forget sometimes that safety is Sam’s flag ship. He’s afraid of losing the only person in his life, in moments like this you get a glimpse of the acute anxiety. It looks exhausting.  

“Alright, your house. But I want dinner.”

“You can have whatever you want.”

Wednesday

“Y/N…” Cole starts, his voice trailing off.

“Yeah?” You don’t look up from the document you’re working on, scribbling a note in red ink. It’s been a long week of case review and making sure that everyone is on the same page. The real work begins in a few days so the team is trying to prep as they can. You’ve been spread out on the small couch in the corner of his office for hours, reviewing and taking notes. Trying to memorize the details.

“I’m gonna say something and I hope you take it the right way, because I’m coming to you from a place of good intentions.”

“That sounds ominous.” Sitting up, you close the folder and place it on the table giving him your full attention. “What’s up?”

“Is he always like that with you?”

“What are you talking about?”

There’s an immediate nervous feeling. A wispy flutter of panic.

“I’m talking about Sam Winchester. He brought you up to his office after you passed out, offered to personally watch over you until a driver was free. He can’t even remember the name of his new assistant but with you he was…attentive.”

“I worked on a project with him last year. We spent a significant amount of time together,” you counter.

_Stay cool._  All this time and Pepper had to walk in on you to see there was something going on. But Cole’s sharp, observant. He picked up on it right away.

Cole stares at you, pursing his lips and trying to decide whether or not to share what he’s really thinking.

“You should watch yourself.” His words are careful. “The way he looks at you, I’ve seen that look before.”

“You’re wrong.” Your entire face is hot. “He’s not like that.”

“I hope you’re right. Just keep my voice in the back of your head, kay? Don’t let yourself be in a situation where you’re alone with him.”

“Cole-”

“I’m serious. He’s interested in you. I’ve known men like him. I wouldn’t want you to be put in a position where something happened. A guy like that is used to getting what he wants. He might not wait for consent.”

That takes you back. The tone shifts and you swallow, thinking about how you want to respond to this curve ball.

“You’re jumping to a lot of conclusions,” you bristle, trying to subdue the urge to put Cole in his place. “Even if he was interested in me, that doesn’t mean he’s a freakin’ rapist.”

“I’m not saying he is.” Cole tries to explain himself. “There’s just something about him. You’re intuitive, you have to feel it too. You have to know the rumors about his brother? How they grew up? You can’t be sure some of that crazy isn’t lurking below the surface-”

“Sam has been nothing but kind to me,” you interrupt. “He’s hard to work for but he’s given me opportunities no one else ever has. You shouldn’t talk about him like that.”

“You don’t wonder why?”

“Why what?” You stand up, taking a step toward the desk. “You don’t think my work is good enough that he would see some talent in me?”

“I didn’t say that, either. You’re smart, articulate, you think on your feet. But that describes most of the employees here. I only meant there could be a reason he singles you out.”

_Fuck._

In four short weeks Cole Trenton has managed to see what no one else could.


	24. Twenty-four

Sam’s zipping around his house like he’s on fire. On any given weekday he doesn’t come home until after eight or nine and works well into the evening. This afternoon however he arrived home just after you and has been wrapping up his day in a frenzy. 

“Damn it,” he snips, shaking his head at a handwritten note. “I can’t read Linda’s handwriting. It’s chicken scratch. I have to get rid of her. I need Pepper back.” 

“I thought her name was Lauren,” you say. 

“Laurel, Lana, I really don’t fucking care.”

“Let me see it.” You pluck the paper from his hand. 

While her handwriting is not the prettiest, it’s still discernible. “Paul Handcock, Steven Turney...no Tunney, and _Lady_ Toni Bevell? Fancy.”

“She’s English,” he snorts. “One of my least favorite people.”

“Who is this a list of?”

“Three execs from the UK I’m bringing over to work on a project. I’ve had an interest in opening an office in London for years now. Legal consultation for international cases.” 

“Wow,” you lean back, watching him tap a message into his phone. “There’s a lot going on behind the scenes.”

“Always,” he sends off a message and takes a breath before going to his laptop. “If everything goes to plan, we’ll be spending some time in London next quarter.”

“We?” you raise an eyebrow.

“Of course,” he types furiously, eyes fixed on the screen. “Unless you don’t want to come with me.”

“No, I mean, I want to. I wasn’t sure you meant you and me.”

“You, me and some of the executive team. It’ll be a lot of work but I can find time to enjoy the city with you.”

Your heart does this school girl flutter at the idea of him automatically including you in his plans. 

“I’d love that.” You glance up to check but he’s not paying attention. “Cole said something interesting today...”

“Oh?”

“He, ah, he said that he’s noticed the way you look at me.” 

Sam pauses, a quiet lull and then he looks at you. “Did he?”

“He said he thinks you’re interested in me and that I shouldn’t be alone with you because you might try something. Might get a little handsy.” Wiggling your fingers you watch for his reaction.  

His nostrils flare, eyes narrowing at this new information. 

“He’s projecting,” Sam quips, stepping closer. “ _He_ watches you, studies you the same way I did. It’s not a bad plan, to set himself up as the ‘good guy’.”

“I don’t think he’s like that.”

“You’re not a man and you don’t have an accurate perception of how attractive you are. Trust me, he’s like that. We all are. It took me all of five minutes to see he was interested in you.” 

“You never said anything.”

“Because I’m not threatened. Unlike Cole’s fictional version of me, I don’t think he’ll lock you in a room and try to feel you up. But he’ll make his play. Give it time.”

“I think you’re both overreacting.” 

“Cole will prove me right eventually,” he grins, tilting his head to the side, looking over your face. “Should I be concerned?”

“No, Mr. Winchester,” you smirk. “But I like that you asked.”

He smiles a controlled little smile and goes back to typing.

“Do you want to order something for dinner? I’m starving.” You’ve been craving a pizza but you doubt you’ll be able to talk Sam into a choice so blatantly unhealthy. 

“We’re going out tonight,” he explains. 

“Where?” you ask. 

“It’s an Italian place, you’ll love it. Carbs as far as the eye can see.”

“Yessss,” you hiss with a laugh and he pulls you into his arms. “Nothing makes me happier than breadsticks.”

“Easy to please,” he kisses you softly, his eyes fluttering shut, then open.  

“We’re going out on a weeknight? This must be a special occasion.”

“Do you know what day it is?” he asks. 

“What?” you look at him, hesitant smile wilting. What have you forgotten? 

“One year ago today you came into my hotel room,” he murmurs. “You were wide-eyed and unsure, but so excited at the same time. I remember exactly what you looked like, sounded like. The way you touched yourself for me.”

How could you possibly forget? It’s been a year and look how far you’ve come. 

“I’d never done anything like that before,” you admit, a shy smile creeping across your face. 

“I hope not,” he nips at your mouth, his lips ghost at the corner of your lips before trailing down to find the curve of your jaw before landing at the shell of your ear and whispering. “We’re going to try a few new things tonight.”

“I’m ready,” you whimper as he sucks at the skin under your ear, sending tiny whizzes of pleasure shooting up and down your spine. Your toes curl in your shoes and you lean into him grasping at his shirt. 

“Glad to hear it,” he murmurs, looking you over in approval. He steps back, leaving you breathless with heavy eyes. “Get dressed.”

\---

“I’ve been looking forward to this part all night,” you confess, standing in his bedroom. 

“I hope it doesn’t disappoint.” 

“I’m not sure that’s even possible,” you say, watching his face awash with amusement and lust. Perhaps a layer of restrained affection underneath it all. 

“Take off your clothes and get on the bed,” Sam instructs. 

You comply without even thinking, stripping your dress off, then your bra and finally the heels that you’re all too happy to get rid of. You crawl on hands and knees to the middle of the bed, wiggling your ass and looking back. Sam walks towards you in nothing but a pair of boxer briefs, a white t-shirt and his tie from earlier in the day. His erection is already straining at the material, and you get a little thrill out of the fact that he wants you this badly. 

“How would you like me, Mr. Winchester?”

“On your back,” he barks, leaning forward to swat you on the ass before you can roll away. With a yelp you lay down on your back, stretching out long as he joins you. Slinging one leg over your belly he straddles your stomach, careful of his weight. “Hands above your head.”

You reached upward, watching his face as he binds your wrists together with his tie and then loops the it through an open slat in the headboard. He’s most comfortable like this, in charge in a sexual situation. He’s also the most handsome just like this, controlled but relaxed, in his element. You wonder what he has in store for you. 

“You’re beautiful tonight,” he comments, dropping down your body, stopping along the journey to suck a nipple into his mouth.

“Just tonight?” You’re not really serious, poking fun and getting lost in the feeling of his mouth sucking hard. 

“Always,” he looks up, dragging his teeth down the skin between your breasts. “But especially tonight.” He snakes lower, kisses his way over your ribs, then belly. “I like taking you out, having other people look at us and knowing you’re mine.”

“I like that too.” You watch as he carefully parts your thighs, his palms pushing your legs wide and you finally realize what’s about to happen.  

He pauses to look up at you, grinning like a cougar about to eat a fat little rabbit and then swoops down, burying his face between your legs. 

“Sam,” you gasp, hips jerking forward. The tip of his nose bumps your clit as his tongue sinks into your folds, searching deeper until he’s shoved as far into your pussy as he can get. Your mind slows down, thick and muddy like warm molasses as he licks inside you. 

Long fingers curl into the clammy flesh under each knee as he pulls you up for him, holding your trembling thighs wide enough that your muscles burn. 

“Fuck, you’re wet,” he mumbles against your cunt, taking a breath before diving back in. Two fingers slide in deep, thrusting slowly in and out. His mouth finds your clit, the tip of his tongue pressing over the aching bud, once, twice and then sucking it into his mouth like he’s been starving for you. 

He’s never gone down on you before. To be honest, you thought this was something he didn’t do. While he’s spent countless hours with his fingers between your thighs he’s never had his mouth on your pussy until now. 

“Tastes so fucking good,” he grunts, mouth pressed up against your sex.  

“Fuck,” you groan, arms tugging at the restraints. 

You can feel him chuckle as his tongue flicks out against hot flesh. He goes gently at first, teasing strokes and lazy circles until you’re ready to climb out of your skin, until you’re threatening to kill him if he doesn’t do _something_ , so he does. Tiny flicks of his tongue against your clit, sliding lower to push inside you with slow thrusts that make you wriggle and writhe and squeal until your hips buck up off the bed and you cum so hard you gush all over his chin. He doesn’t stop there, pushing harder, thrusting deeper, licking up inside your cunt until you’re squirming and cooing against him. 

When you finally can’t take anymore, he rises and tugs at the tie around your wrists, freeing your arms. Then he rests back on his haunches before getting to his knees to pull his shirt up over his head, throwing it to the floor. Reaching he starts to push down his underwear, and then just stops, looking down at you with eyes that linger, take their time, tracing every inch of your bare skin, like a kid on Christmas morning. 

“You’re mine,” he breathes, then nods in summation. 

“Yes, I am yours.” You reach out for him, and he ducks down to all fours over you with a grin, kisses your cunt again just to watch you squirm, and then he slides his body up, over yours, skin sticky and slipping with sweat.

He kisses you, tongue diving deep, and you can taste herself on him, thick spice that permeates your senses, and you dig your nails into his bare back, clutching him close.

“You still have too many clothes on,” you whisper into his ear, biting down on the lobe.

He hisses and rolls his hips against you, and you can feel his cock, diamond hard inside his boxers, pushing into your clit, and oh, God, yes, more of _that_ please. 

He kicks out of his underwear like a snake shedding its skin, and it’s a beautiful thing, really, something you’d take a lot more time to appreciate if you didn’t need him to fuck you so badly right now.

When he’s naked, he lays back down on top of you, chest to chest, belly to belly, you can feel his heartbeat, feel him breathe, and you realize you’re trembling just a little. He wraps his arms around you, and you can feel him, just right, hardness pushing against where you’re so hot and slick and needing.

He slides inside, slow, and God, so full, so tight, nothing’s ever been this full or this sweet, and you’re digging your nails into his back, crying out against the thin line of pleasure. He dips his head to swallow your cry with his mouth, pushing further inside, sinking deeper until you can feel him rest against your body.

“Hey,” he whispers, and your eyes flutter open, find his. They’re dark, so dark with lust and need and bright with fire, so beautiful. God he’s so fucking beautiful. He’s not sure what this reaction is. Neither are you. This feels like connection, like more than anything that came before. You’re shaking like a virgin getting fucked for the first time. “You alright?”

“God, yes,” you moan and twist your hips against him, feel him shudder. “Please, Sam. Fuck me.” You push up with your body, wanting more, needing him to move.

But he doesn’t. He just stays there, still and stunned and staring down at you for a moment, the humid, heavy weight of his breath against your jaw ceasing for an instant. And you don’t understand why he isn’t moving. 

And then he remembers to breathe, catches your chin between his teeth, twists his head and slides his mouth up over yours. He pulls back, and you can feel the sweet slide of his cock as it draws out of you, almost to the tip, and you’re whimpering, clinging, trying to find him with your hips. Then he thrusts into you with a quick roll of his hips, rushing to fill the empty space inside your pussy and you’re moving to meet him, head thrown back and soft cries pouring from open lips in a flood.

You rock and twist together, one of his hands holding yours and the other on your breast, pinching and rolling the nipple between his fingers, mouth murmuring a stream of words into your throat, and you’re gripping his ass in your hand, moving with him, urging him on faster until it all dissolves into delicious friction and taste of salty, sticky skin, mouths and hands tasting and touching each other everywhere they can reach. Until at last, your mouths fuse together and you find his hands with yours, lace small fingers through his thick ones and hold on tight, biting down hard against his lower lip for an instant as you shudder, careening toward the edge.

“Can I cum?” you wheeze, the words fractured. 

“Yes,” he whispers, grabbing you by the shoulders to hold you still, thrusting harder, his eyes locked on yours. “That’s it. Cum for me. Wanna see it.”

“Fuck,” you mutter hoarsely, and then cum so hard your teeth snap together and it’s all you can do to hold on to him.

“So fucking hot, tight, Jesus Christ I can feel you,” Sam grates out, biting hard against your jaw, and then his fingers clutch deep into your shoulders, convulsing, and you can feel his whole body tense and shudder, feel his cock flex and empty inside you.  

He relaxes against you, his weight pressing against you comfortably, head resting in the space between your neck and shoulder as he catches his breath. You turn your face into him, cheek brushing against his hair, and smile, still breathing hard and humming with pleasure. You flex your hands, still holding tight to his, and he lifts his head to look at you, grinning down at you with an exhausted but pleased look. 

“Not our usual sex but…” he trails off, looking boyishly handsome with a wild cap of hair. He’s rumpled and self-satisfied, and you suppose he’s got every right to be after making you cum like that. Twice.   

“It was amazing,” you smile up at him. “You always know what I need, even when I don’t.”

He studies you for a moment, eyes twinkling before leaning in to kiss you. 

-

“What were you like?” you ask, settling into his side. “When you were a kid I mean. What did little Sam want to grow up to be?”

First comes Sam’s trademark pause and then a simple confession that tells you so much more. 

“I just wanted to be normal. As a kid, I was starving for it. I wanted to have a house and a mom, I wanted my dad to sit down with Dean and I every night and eat dinner. Chasing monsters was the last thing on my mind, what I craved was to fade into the background. To fit in. And now look at me. If ten year old Sam could see me now he’d be appalled.”

“Why?” you murmur, the pads of your fingers rubbing a gentle path through his chest hair. “You’re successful, you don’t think he’d be proud?” 

“Yeah, but that wasn’t the plan. My dad lost himself in work and I swore up and down I’d never be like that. I wanted a family, a dog, a nine-to-five job. I’ve gone so far in the other direction I couldn’t be further from normal.” 

“Is there any part of your family that you miss?”

“I don’t know,” he replies immediately, shifting his hips. 

“There’s nothing good from all those years?”

“Dean, I suppose.” His hand trails over the back of your elbow and up your arm. “We butted heads from the time I could talk but he took care of me. He did the best he could. Dad would leave and Dean was in charge. When my dad first started leaving us on our own it was only for a night or two. But as I got older he’d leave for a week, sometimes two. Dean fed me, got me to school, stole the best comic books so I’d have something to keep me busy.”

“That’s a lot...for both of you.” 

Your heart sinks into your gut as you picture these two little kids alone in some skeezy motel. It’s a wonder Sam got from there to here. 

“I felt guilty for a long time after I left. For years I wondered if I’d done the right thing. I kept Dean grounded, or tried to anyway. But when Jess died I…”

He trails off. 

“I’d like to know about her,” you add. Tilting your head up you burrow into his neck and use the arm over his chest to pull yourself closer to his body heat. “Only if you want to tell me.”

“I don’t talk about her.” He clears his throat. 

“Okay.” 

The two of you lay there listening to the distant ticking of the wall clock in the hallway. His house is unnaturally quiet, a modern capsule, sealed off from the rest of the world. 

The minutes tick by as you lay there, both of you wide awake but neither willing to break the bubble. You’re about to suggest a shower when he speaks again. 

“She baked all the time,” he says. “She was good at it. Cookies, pastries, cakes. I gained ten pounds during our first year together.” 

You don’t respond, just wait as his fingers curl into your hair. 

“She was the first person in my life to ever encourage me to do the things _I_ wanted. Every time I suggested something she’d tell me to go for it. My whole life my dad told me I needed to be like him, there was no other choice. But she encouraged me to be anything I wanted.” 

Again, you’re silent. Afraid of intruding on this fragile moment of reflection. 

“She loved me and I lied to her. I made up stories about my family. I told her my dad was dead. My brother was a drunk. Anything to avoid talking about them. I rewarded her affection with made-up stories because I didn’t want to own up to where I came from. Looking back it was stupid, she wouldn’t have cared. We could have truly known each other and I took that opportunity away from us.” He sighs. “I won’t make the same mistake with you. I can’t talk about it all, not with you, not with anyone. But I won’t ever lie to you.” 

“Me either,” you confirm. “We all need things that are ours alone. Secrets, moments, even people sometimes. I don’t begrudge you that.”

“You always surprise me,” he says, deadpan and devoid of emotion. “You deserve a better man than me. Someone who’s not broken, gutted from the inside. You deserve to be loved.”

You think about those words, _you deserve to be loved._ As if he’ll never be able to deliver. 

“You don’t think you’ll ever be able to love me?” you ask. 

He grunts, clearly uncomfortable but his arms only tighten around you. 

“I hope I can. You make me feel a lot of emotions, strong emotions...my first instinct is to purge them. Ignore them before they grow stronger. I have a lot to work on.”

“I could love you,” you respond, but the untruth of the statement doesn’t settle right. You’ve felt it for weeks now. Refusing to give in to fear you say what you feel. “I do love you.”

You hold your breath. Will he run? Kick you out? The truth is that you love him but you still don’t trust him, not completely. 

“I’m not sure how you could love a person like me. I’m a shell, half-empty inside,” he responds calmly. 

“I don’t think that’s true. You shut off access to certain parts of yourself, but they still exist. Empathy, compassion, love... I've seen little glimpses of all of them.”

He snorts.

“What?” you ask. 

“A little voice in the back of my head keeps whispering there’s a good chance that you like the way I make your body feel and that’s all this will ever be.”

It’s easy to forget that Sam doubts himself. But he’s just human after all and he needs assurances just like everyone else. 

“I do like the way you make me feel. The way you touch me. But I also like the way you look at me, listen to me, really listen. You care what I think. I like how you think I’m capable of more professionally, you don’t let me fade into the background, you challenge me. I like laying here with you in the dark. I like listening to you. The sex is amazing, but it’s sex. There’s so much more to being together.”

There’s a flickering burst of light from outside and the low boom of a storm approaching. Sam doesn’t respond, he just holds you close, fingers trailing over skin as words and confessions sink in. It’s impossible to know what the future holds. But right now you have each other and neither of you are taking that for granted. 

-

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